Acetic Acid → (3R*,4S*)-4-Benzylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

HRID 1511792

反応式

HRID 1511792 の反応式
[CH2:1]([O:3][C:4]([CH:6]1[C:10](=O)[CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5])[CH3:2].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(O)=O.C([BH3-])#N.[Na+]>CCO>[CH2:1]([O:3][C:4]([C@H:6]1[C@H:10]([NH:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5])[CH3:2]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 108689421-tert-Butyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate

生成物 1

HCID 68028622(3R*,4S*)-4-Benzylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester収率 54%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of (RS)-4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (commercial; 1 g, 3.9 mmol) in EtOH (15 mL) were added benzylamine (0.85 mL, 7.77 mmol) and AcOH (0.45 mL, 7.77 mmol) and the mixture was stirred 3 h at rt. Sodium cyanoborohydride (0.98 g, 15.5 mmol) was then added at rt and the mixture was heated to 75° C. for 5 h, then 15 h to 50° C. and again 1 h to 75° C. The mixture was concentrated under reduced pressure, water was added and the mixture extracted 3× with EA. The combined org. extracts were washed with brine dried over MgSO4 and concentrated under reduced pressure. The residue was purified by CC (Hep/EA from 2:1 to 1:1) to afford the title intermediate as a yellow oil (0.73 g, 54%).

後処理

  1. temperaturethe mixture was heated to 75° C. for 5 h
  2. concentrationThe mixture was concentrated under reduced pressure, water
  3. additionwas added
  4. extractionthe mixture extracted 3× with EA
  5. washextracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by CC (Hep/EA from 2:1 to 1:1)

出典と根拠

ORDレコード
ord-48dd7f9be9884fb39e7af3737731e561
出典データセット
uspto-grants-2012_07
特許番号
US08217029B2

関連ノート

読み込み中…