Diisopropylamine → rac-(3S,4R)-[4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

HRID 527470노트

반응식

HRID 527470 반응식
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:11][N:10](CC2C=CC=CC=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(NC(C)C)(C)C.C(OC(Cl)C)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 7912DiisopropylamineHCID 153309271-ChloroethylformateHCID 67237396rac-(3S,4R)-[1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 67237824rac-(3S,4R)-[4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester수율 153%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of rac-(3S,4R)-[1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (5.59 g, 0.013 mol) and N,N-diisopropylamine (6.81 mL, 0.017 mol) in toluene (60 mL) was added at ambient temperature 1-chloroethyl formate (1.88 mL, 0.017 mol) and the reaction mixture was stirred for 24 h. It was concentrated and the resulting residue was diluted in methanol (60 mL) and stirred for 3 h at ambient temperature. Concentration afforded the crude title compound (6.59 g, 67% purity) as a light brown solid which was directly used without further purification.

후처리

  1. concentrationIt was concentrated
  2. additionthe resulting residue was diluted in methanol (60 mL)
  3. stirringstirred for 3 h at ambient temperature
  4. concentrationConcentration

출처 및 근거

ORD 기록
ord-adee08ad31424aa8aae613e34fc3fc3c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346786B2

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