Tributylstannane → methyl 2-[(3S,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

HRID 851400노트

반응식

HRID 851400 반응식
C([SnH](CCCC)CCCC)CCC.[OH:14][C:15]([C@:18]1([N+]#[C-])[C@@H:21]([CH2:22][CH:23]=[CH2:24])[N:20]([C:25](=[C:30]([CH3:32])[CH3:31])[C:26]([O:28][CH3:29])=[O:27])[C:19]1=[O:33])([CH3:17])[CH3:16].N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[OH:14][C:15]([C@@H:18]1[C@@H:21]([CH2:22][CH:23]=[CH2:24])[N:20]([C:25](=[C:30]([CH3:32])[CH3:31])[C:26]([O:28][CH3:29])=[O:27])[C:19]1=[O:33])([CH3:17])[CH3:16]

참가 물질

5

반응물 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 53962359methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

생성물 1

HCID 22823199methyl 2-[(3S,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate수율 96.6%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

Tributyltin hydride (0.707 ml) was added to a mixture of methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (630 mg) and azobisisobutyronitrile (34 mg) in benzene (6 ml) at room temperature, and the mixture was refluxed for 15 minutes. The reaction mixture was cooled and chromatographed on silica gel (20 g) eluting with a mixture of hexane and ethyl acetate (3:1-1:1) to give a 3:1 mixture (559 mg) of methyl 2-[(3S,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate and its (3R,4R)-isomer.

후처리

  1. temperaturethe mixture was refluxed for 15 minutes
  2. temperatureThe reaction mixture was cooled
  3. customchromatographed on silica gel (20 g)
  4. washeluting with a mixture of hexane and ethyl acetate (3:1-1:1)

출처 및 근거

ORD 기록
ord-cea6e7d14a4e4e738914965863aa760c
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04383945

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