Sodium triacetoxyborohydride → 1-(5-Bromo-2-chloro-benzyl)azetidine-3-carboxylic acid tert-butyl ester

HRID 1629747노트

반응식

HRID 1629747 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=O.Cl.[C:12]([O:16][C:17]([CH:19]1[CH2:22][NH:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(Cl)Cl>[C:12]([O:16][C:17]([CH:19]1[CH2:20][N:21]([CH2:7][C:6]2[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[Cl:10])[CH2:22]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

참가 물질

6

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 106089255-Bromo-2-chlorobenzaldehydeHCID 67346984tert-Butyl azetidine-3-carboxylate hydrochloride

생성물 1

HCID 583744221-(5-Bromo-2-chloro-benzyl)azetidine-3-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

실험 절차

A mixture of 5-bromo-2-chloro-benzaldehyde (2 g, 9.11 mmol) and azetidine-3-carboxylic acid tert-butyl ester hydrochloride (1.765 g, 9.11 mmol) in dichloroethane (50 mL) was stirred at room temperature for 10 minutes. To this mixture was added sodium triacetoxy-borohydride (3.86 g, 18.23 mmol) in 3 portions over a period of 10 minutes and the cloudy mixture was stirred overnight. The reaction mixture was diluted with CH2Cl2 (100 mL) and washed twice with 10% sodium bicarbonate solution, twice with water then brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude was purified by chromatography on silica gel (cyclohexane/EtOAc).

후처리

  1. stirringthe cloudy mixture was stirred overnight
  2. washwashed twice with 10% sodium bicarbonate solution, twice with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified by chromatography on silica gel (cyclohexane/EtOAc)

출처 및 근거

ORD 기록
ord-61c9ca146a9b43c2a3e4ff852a0bb7a1
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791100B2

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