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 456756노트

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HRID 456756 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: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]

참가 물질

5

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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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-907e8e50039a433e87f4b9e7df54670e
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186731B2

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