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

HRID 40578

反応式

HRID 40578 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-59d2975d85a348a1993e3f7f99008638
出典データセット
uspto-grants-2013_09
特許番号
US08530476B2

関連ノート

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