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

HRID 45505노트

반응식

HRID 45505 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-65ddf8eec5324a6489848dea4680643a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541461B2

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