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

反応式

HRID 456769 の反応式
[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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 152122Dirhodium tetraacetate触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-51bbb9dac8cb40188705d3fc55dd6c59
出典データセット
uspto-grants-2007_03
特許番号
US07186731B2

関連ノート

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