Citric Acid → tert-Butyl (1R,3S,4S,6S)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

HRID 456756ノート

反応式

HRID 456756 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:13](=[O: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].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[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]

参加物

5

反応物 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 86598907tert-Butyl (1R,3S,4S)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

生成物 1

HCID 86598908tert-Butyl (1R,3S,4S,6S)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate収率 101.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl (1R,3S,4S)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 22-1 (80 mg) in methanol (8 mL), was added sodium borohydride (1 mg). The mixture was stirred at 0° C. for 1 hr. To the reaction mixture, was added citric acid solution. The mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was triturated with ether to give the target compound (82 mg) as a solid.

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-907e8e50039a433e87f4b9e7df54670e
出典データセット
uspto-grants-2007_03
特許番号
US07186731B2

反応ノート

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