Water → 4-[2,2-Bis-(4-chloro-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 45505ノート

反応式

HRID 45505 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:9]=O)=[CH:4][CH:3]=1.[C:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C([BH3-])#N.[Na+].O>CO>[C:21]([O:20][C:18]([N:25]1[CH2:30][CH2:29][N:28]([CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:27][CH2:26]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

参加物

6

反応物 4

HCID 962WaterHCID 143452tert-Butyl piperazine-1-carboxylateHCID 167694Bis(4-chlorophenyl)acetaldehydeHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 593319524-[2,2-Bis-(4-chloro-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester収率 11.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of bis-(4-chloro-phenyl)-acetaldehyde (3.74 mmol) in methanol under a nitrogen atmosphere, N—BOC-piperazine (1.05 g, 5.61 mmol) was added, the reaction mixture was stirred for 1 hour before addition of sodium cyanoborohydride (0.28 g, 4.49 mmol). The reaction mixture was stirred for 18 hours, water added (3 ml) and the solvent removed under reduced pressure. The residue was partitioned between dichloromethane and water, the organic layer was separated, dried (MgSO4), filtered and concentrated. Purified over flash silica chromatography eluting with ethyl acetate/petroleum ether (3:7) to yield the title compound (0.18 g, 11% yield for steps 30A and 30B combined). LC/MS: (PS-A2) Rt 2.66 [M-BOC+H]+ 335.02.

後処理

  1. customthe solvent removed under reduced pressure
  2. customThe residue was partitioned between dichloromethane and water
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurified over flash silica chromatography
  8. washeluting with ethyl acetate/petroleum ether (3:7)

出典と根拠

ORDレコード
ord-65ddf8eec5324a6489848dea4680643a
出典データセット
uspto-grants-2013_09
特許番号
US08541461B2

反応ノート

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