Potassium Hydroxide → 4-(3,4-Dibromo-benzyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 40578

반응식

HRID 40578 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Br:23])[CH:18]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[K+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:18][C:17]2[CH:20]=[CH:21][C:22]([Br:23])=[C:15]([Br:14])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 14797Potassium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 6220533,4-DibromobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 578808894-(3,4-Dibromo-benzyl)-piperazine-1-carboxylic acid tert-butyl ester수율 73.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of piperazine-1-carboxylic acid tert-butyl ester (3.5 g) and 3,4-dibromobenzaldehyde (5.0 g) in DCM (80 mL) was treated with NaB(OAc)3H (5.6 g). After 16 h, the resulting mixture was treated with 10% aq. KOH (80 mL). The aqueous phase was extracted with DCM (1×80 mL). The organic extracts were combined and dried (MgSO4). Most of the solvent was removed by concentration. Upon standing overnight, the resulting mixture produced crystals that were filtered and washed with DCM (1×5 mL), giving the title compound as a white crystalline solid (6.0 g).

후처리

  1. extractionThe aqueous phase was extracted with DCM (1×80 mL)
  2. dry with materialdried (MgSO4)
  3. customMost of the solvent was removed by concentration
  4. waitUpon standing overnight
  5. customthe resulting mixture produced crystals that
  6. filtrationwere filtered
  7. washwashed with DCM (1×5 mL)

출처 및 근거

ORD 기록
ord-59d2975d85a348a1993e3f7f99008638
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530476B2

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