Tert-butyl 2-diazoacetate → tert-Butyl (1R,3S,4S,6R)-6-(2-tert-butoxy-2-oxoethoxy)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-2-azabicyclo[2.2.1]heptane-2-carboxylate

HRID 456769

반응식

HRID 456769 반응식
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([OH:17])[CH2:14]2)[N:11]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:9])#[N:2].[N+](=[CH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[N-]>ClCCl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[C:31]([O:30][C:28](=[O:29])[CH2:27][O:17][C@H:13]1[C@H:12]2[CH2:16][C@H:15]([C@@H:10]([C:8]([N:4]3[CH2:5][CH2:6][CH2:7][C@H:3]3[C:1]#[N:2])=[O:9])[N:11]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1)([CH3:34])([CH3:33])[CH3:32]

참가 물질

5

반응물 2

HCID 5097903Tert-butyl 2-diazoacetateHCID 86598896tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

생성물 1

HCID 86598921tert-Butyl (1R,3S,4S,6R)-6-(2-tert-butoxy-2-oxoethoxy)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-2-azabicyclo[2.2.1]heptane-2-carboxylate

시약·촉매·용매 2

HCID 152122Dirhodium tetraacetate촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 5-7 (322 mg) in dichloromethane (6 mL), were added rhodium acetate dimer (4.24 mg) and tert-butyl diazoacetate (0.27 mL). The mixture was stirred at room temperature for 4 hrs. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate to give the target compound (236 mg).

후처리

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-51bbb9dac8cb40188705d3fc55dd6c59
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186731B2

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