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

HRID 338961ノート

反応式

HRID 338961 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fe7a72db9372468bb8044420d59b58d4
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

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