Water → Tert-Butyl 4-{2-[(1S)-1-(Acetylamino)Ethyl]-4-Chlorophenyl}Piperidine-1-Carboxylate

HRID 644954노트

반응식

HRID 644954 반응식
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C@H:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[CH3:7].C(N(CC)CC)C.O>C(Cl)Cl>[C:1]([NH:5][C@H:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:17][CH2:16]1)[CH3:7])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68518377Tert-Butyl 4-{2-[(1S)-1-Aminoethyl]-4-Chlorophenyl]Piperidine-1-Carboxylate

생성물 1

HCID 11668043Tert-Butyl 4-{2-[(1S)-1-(Acetylamino)Ethyl]-4-Chlorophenyl}Piperidine-1-Carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Acetyl chloride (1.71 mL, 24.0 mmol) was added to a solution crude tert-butyl 4-{2-[(1S)-1-aminoethyl]-4-chlorophenyl}piperidine-1-carboxylate (5.42 g of ˜70% pure material, 11.2 mmol) and triethylamine (6.69 mL, 48.0 mmol) in methylene chloride at approximately 0° C. After 2 h, the reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 35-50% ethyl-acetate/hexanes as eluent) provided tert-butyl 4-{2-[(1S)-1-(acetylamino)ethyl]-4-chlorophenyl}piperidine-1-carboxylate as a pale yellow foam. If desired, traces of the minor R-enantiomer could be removed using preparative chiral high pressure liquid chromatography on CHIRALPAK AD Phase (7.5% ethanol/heptanes as eluent) to give in order of elution: R-enantiomer as a colorless solid followed by the S-enantiomer as a colorless solid.

후처리

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 35-50% ethyl-acetate/hexanes as eluent)

출처 및 근거

ORD 기록
ord-be0aab309d164dbc88b5497042c1cc93
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700778B2

반응 노트

불러오는 중…