Trifluoroacetic acid → Benzyl N-[(3R,4R)-4-hydroxypyrrolidin-3-YL]carbamate

HRID 338961노트

반응식

HRID 338961 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@H:16]([OH:17])[CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:17][C@@H:16]1[CH2:15][NH:14][CH2:13][C@H:12]1[NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 57970124trans-Tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 68219095Benzyl N-[(3R,4R)-4-hydroxypyrrolidin-3-YL]carbamate수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3R,4R)-tert-butyl 3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (4.91 g, 14.60 mmol) in DCM (20 mL) was added TFA (11.25 mL, 146.0 mmol) and the mixture was stirred at ambient temperature for 1 hour. The solvent was removed under reduced pressure. 6 N HCl in water (10 mL) was added. The mixture was stirred at ambient temperature for 30 minutes and neutralized with saturated sodium bicarbonate to about pH 8. It was extracted with DCM:IPA=4:1 (50 mL). The organic layer was separated, dried (sodium sulfate), filtered and concentrated under reduced pressure to give benzyl (3R,4R)-4-hydroxypyrrolidin-3-ylcarbamate (2.45 g, 71.0%) as a solid.

후처리

  1. customThe solvent was removed under reduced pressure
  2. addition6 N HCl in water (10 mL) was added
  3. stirringThe mixture was stirred at ambient temperature for 30 minutes
  4. extractionIt was extracted with DCM
  5. customThe organic layer was separated
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fe7a72db9372468bb8044420d59b58d4
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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