2,4-Dichlorobenzaldehyde → (S)-tert-Butyl 3-((2,4-dichlorobenzyl)amino)pyrrolidine-1-carboxylate

HRID 252085

반응식

HRID 252085 반응식
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[Cl:28][C:29]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:30]=1[CH:31]=O>ClCCCl.ClCCl>[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][C@H:24]([NH:27][CH2:31][C:30]2[CH:33]=[CH:34][C:35]([Cl:37])=[CH:36][C:29]=2[Cl:28])[CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

참가 물질

6

반응물 3

HCID 134042,4-DichlorobenzaldehydeHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 66854615(S)-tert-Butyl 3-((2,4-dichlorobenzyl)amino)pyrrolidine-1-carboxylate수율 46.4%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

Alternatively, add sodium triacetoxyborohydride (1.6 g, 7.6 mmol) to a mixture of (S)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester (1 g, 5.4 mmol) and 2,4-dichlorobenzaldehyde (2.8 g, 16.2 mmol) in 1,2-dichloroethane (10 mL) and stir overnight at room temperature. Dilute with dichloromethane and wash with saturated aqueous sodium chloride, dry (magnesium sulfate) concentrate and chromatograph on silica gel to give (S)-3-(2,4-dichlorobenzylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (865 mg, 33%). 1H NMR (400 MHz, CDCl3) 7.33-7.38 (2H, m), 7.23 (1H, d, J=7.82 Hz), 3.85 (2H, d, J=1.96 Hz), 3.45-3.56 (2H, m), 3.30-3.40 (2H, m), 3.19-3.10 (1H, m), 2.04 (1H, m), 1.74 (1H, m), 1.46 (9H, s), MS (ES): m/z=345 [M+].

후처리

  1. washwash with saturated aqueous sodium chloride
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate

출처 및 근거

ORD 기록
ord-fe6f6a67c45741deb82c820dec456437
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868014B2

연결된 노트

불러오는 중…