IPC분류정보
국가/구분 |
United States(US) Patent
등록
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국제특허분류(IPC7판) |
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출원번호 |
US-0482036
(2009-06-10)
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등록번호 |
US-8227611
(2012-07-24)
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발명자
/ 주소 |
- Cantrell, Gary L.
- Magparangalan, Dan P.
- Moser, Frank W.
- Bao, Jian
- Grote, Christopher W.
- Wang, Peter X.
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출원인 / 주소 |
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인용정보 |
피인용 횟수 :
0 인용 특허 :
3 |
초록
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The present invention is directed to processes for the synthesis of morphinans. In particular, a process for the asymmetric reduction of an imine moiety in a 3,4-dihydroisoquinoline to produce a tetrahydroisoquinoline, followed by a Birch reduction to produce a hexahydroisoquinoline. In various embo
The present invention is directed to processes for the synthesis of morphinans. In particular, a process for the asymmetric reduction of an imine moiety in a 3,4-dihydroisoquinoline to produce a tetrahydroisoquinoline, followed by a Birch reduction to produce a hexahydroisoquinoline. In various embodiments, the 3,4-dihydroisoquinoline contains a phenol moiety protected with a labile protecting group. In other embodiments, the imine reduction reaction mixture contains silver tetrafluoroborate.
대표청구항
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1. A compound corresponding to Formula 703: wherein R1 and R7 are independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR111;R2 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR211;R3 is hydrogen, hydrocarbyl, or —OR311;R4 is hydrogen, hydrocarbyl, substituted hydrocarbyl
1. A compound corresponding to Formula 703: wherein R1 and R7 are independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR111;R2 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR211;R3 is hydrogen, hydrocarbyl, or —OR311;R4 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR411;R5 and R6 are independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR511;R12 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR121; R13 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR511;R17 is hydrogen, or acyl;R111 is hydrogen, hydrocarbyl, or substituted hydrocarbyl;R211 is hydrogen, hydrocarbyl, —C(O)R212, —C(O)NHR213, or —SO2R214;R212, R213 and R214 are independently hydrocarbyl or substituted hydrocarbyl;R311 is hydrogen, hydrocarbyl, —C(O)NHR313, or —SO2R314;R313, or R314 are independently hydrocarbyl or substituted hydrocarbyl;R411 is hydrogen, hydrocarbyl, —C(O)R412, —C(O)NHR413, or —SO2R414;R412 is hydrogen, alkyl or aryl, provided, R412 is other than phenyl;R413, and R414 are independently hydrocarbyl or substituted hydrocarbyl;R511 is hydrogen, hydrocarbyl, or substituted hydrocarbyl;R121 is hydrogen, hydrocarbyl, or substituted hydrocarbyl; andwherein at least one of R2, R3, or R4 is —OC(O)R212, —OC(O)NHR213,—OSO2R214, —OC(O)R313, —OSO2R314, —OC(O)R412, —OC(O)NHR413, or —OSO2R414. 2. The compound of claim 1, wherein: R2 is —OR211;R211 is hydrogen, alkyl, —C(O)R212, —C(O)NHR213, or —SO2R214; andR212, R213, and R214 are independently alkyl or aryl. 3. The compound of claim 1, wherein: R3 is —OR311;R311 is hydrogen, alkyl,—C(O)NHR313, or —SO2R314; andR313, and R314 are independently alkyl or aryl. 4. The compound of claim 1, wherein: R4 is —OR411;R411 is hydrogen, alkyl, —C(O)R412, —C(O)NHR413, or —SO2R414; andR413, and R414 are independently alkyl or aryl. 5. The compound of claim 1, wherein R12 is alkyl, allyl, benzyl, or halo. 6. The compound of claim 1, wherein R212, R213, R214,R313, R314, R412, R413, and R414 are methyl. 7. The compound of claim 1, wherein R3 is methoxy, R4 is —OC(O)CH2CH3, or —OSO2CH3, R6 is methoxy, and R1, R2, R5, R7, R12, R13 are hydrogen. 8. The compound of claim 1, wherein: R2 is —OR211;R211 is hydrogen, alkyl, —C(O)R212, —C(O)NHR213, or —SO2R214; andR212, R213, and R214 are independently alkyl or aryl;R3 is —OR311, R311 is hydrogen, alkyl, —C(O)NHR313, or —SO2R314; andR313, and R314 are independently alkyl or aryl;R4 is —OR411;R411 is hydrogen, alkyl, —C(O)R412, —C(O)NHR413, or —SO2R414; andR413, and R414 are independently alkyl or aryl. 9. The compound of claim 8, wherein R212,R213, R214,R313, R314, R412, R413, and R414 are methyl; R3 is methoxy, R4 is —OC(O)CH2CH3, or OSO2CH3, R6 is methoxy, and R1, R2, R5, R7, R12, R13 are hydrogen.
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