Acetic Acid → (2S,4S)-4-fluoro-1-(2-hydroxyacetyl)pyrrolidine-2-carbonitrile

HRID 606715노트

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HRID 606715 반응식
[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:17])[CH2:8][O:9][Si](C(C)(C)C)(C)C)[C@H:4]([C:18]#[N:19])[CH2:3]1.O.C(O)(=O)C>O1CCCC1>[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:17])[CH2:8][OH:9])[C@H:4]([C:18]#[N:19])[CH2:3]1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 962WaterHCID 67053339(2S,4S)-4-fluoro-1-[2-(tert-butyldimethylsilyloxy)acetyl]pyrrolidine-2-carbonitrile

생성물 1

HCID 67053346(2S,4S)-4-fluoro-1-(2-hydroxyacetyl)pyrrolidine-2-carbonitrile수율 96.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

(2S,4S)-4-fluoro-1-[2-(tert-butyldimethylsilyloxy)acetyl]pyrrolidine-2-carbonitrile (5.50 g) was dissolved in tetrahydrofuran (37 mL). To this solution, water (37 mL) and acetic acid (115 mL) were sequentially added and the mixture was stirred at 50° C. for 7.5 hours and then at 70° C. for 9 hours. Subsequently, the reaction mixture was concentrated under reduced pressure and the resulting pale brown tar-like residue was triturated with diethyl ether. The resulting solid was collected by filtration and dried under reduced pressure to give (2S,4S)-4-fluoro-1-(2-hydroxyacetyl)pyrrolidine-2-carbonitrile as a pale brown solid (3.19 g).

후처리

  1. waitat 70° C. for 9 hours
  2. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  3. customthe resulting pale brown tar-like residue was triturated with diethyl ether
  4. filtrationThe resulting solid was collected by filtration
  5. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-fa379d84b0304b3da7ee545f642da20c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915427B2

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