Benzylamine → (2S,3S,5R)-2-benzyl-3-benzylamino-5-ethyl-pyrrolidine-1-carboxylic acid isopropyl ester

HRID 409466노트

반응식

HRID 409466 반응식
[CH:1]([O:4][C:5]([N:7]1[CH:11]([CH2:12][CH3:13])[CH2:10][C:9](=O)[C@@H:8]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:6])([CH3:3])[CH3:2].[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH4-].[Na+]>CO.O.[OH-].[Na+].CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:1]([O:4][C:5]([N:7]1[C@H:11]([CH2:12][CH3:13])[CH2:10][C@H:9]([NH:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@@H:8]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:6])([CH3:3])[CH3:2]

참가 물질

8

반응물 3

HCID 7504BenzylamineHCID 4311764Sodium borohydrideHCID 59614420(2S)-2-benzyl-5-ethyl-3-oxo-pyrrolidine-1-carboxylic acid isopropyl ester

생성물 1

HCID 59614354(2S,3S,5R)-2-benzyl-3-benzylamino-5-ethyl-pyrrolidine-1-carboxylic acid isopropyl ester수율 55.3%

시약·촉매·용매 4

HCID 11026Titanium isopropoxide촉매HCID 887Methanol용매HCID 962Water용매HCID 14798Sodium Hydroxide용매

실험 절차

To a solution of a diastereomeric mixture of (2S)-2-benzyl-5-ethyl-3-oxo-pyrrolidine-1-carboxylic acid isopropyl ester (0.29 mmol; 84 mg) and benzylamine (0.58 mmol; 62.1 mg) in MeOH (1.5 mL) is added titanium(IV) isopropoxide (0.58 mmol; 165 mg) at room temperature under nitrogen. After stirring for 5 hours, NaBH4 (0.58 mmol; 22 mg) is added to the mixture at 0° C. The mixture is stirred for 2 hours at room temperature and then diluted with water and aqueous 0.1 M NaOH solution. The solution is filtered and concentrated under reduced pressure. To the residue is added water and dichloromethane. The product is extracted twice with dichloromethane. The combined organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (n-hexane/EtOAc) to give (2S,3S,5R)-2-benzyl-3-benzylamino-5-ethyl-pyrrolidine-1-carboxylic acid isopropyl ester (61 mg, 55%); ESI-MS m/z: 381 [M++1], Retention time 1.77 min (condition A).

후처리

  1. stirringThe mixture is stirred for 2 hours at room temperature
  2. filtrationThe solution is filtered
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue is added water and dichloromethane
  5. extractionThe product is extracted twice with dichloromethane
  6. washThe combined organic layer is washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by column chromatography on silica gel (n-hexane/EtOAc)

출처 및 근거

ORD 기록
ord-13b6a57c964d4eecaaa4021f11b4d010
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759365B2

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