Benzyl Alcohol → tert-Butyl [{1-(2-benzyloxycarbonyl-2-methylpropyl)piperidin-4-yl}methyl]carbamate

HRID 645988

반응식

HRID 645988 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.Cl[CH2:17][C:18]([CH3:30])([CH3:29])[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].ClCC(C)(C)C(Cl)=O.C(O)C1C=CC=CC=1.C(N(C(C)C)C(C)C)C.[I-].[Na+]>CN(C)C=O>[C:11]([O:10][C:9](=[O:15])[NH:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([CH2:30][C:18]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])([CH3:17])[CH3:29])[CH2:2][CH2:3]1)([CH3:12])([CH3:14])[CH3:13]

참가 물질

8

반응물 6

HCID 244Benzyl AlcoholHCID 5238Sodium IodideHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 81531DiisopropylethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 54294282Benzyl 3-chloropivalate

생성물 1

HCID 86602121tert-Butyl [{1-(2-benzyloxycarbonyl-2-methylpropyl)piperidin-4-yl}methyl]carbamate수율 1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

To a stirred solution of tert-butyl (piperidin-4-ylmethyl)carbamate (38.8 g, 181 mmol) in N,N-dimethylformamide (100 mL) was added benzyl 3-chloropivalate (14.2 g, 124 mmol, prepared from 3-chloropivaloyl chloride (25.6 g, 165 mmol) and benzyl alcohol (19.6 g, 181 mmol), ethyldiisopropylamine (64.0 g, 495 mmol) and sodium iodide (27.1 g, 181 mmol) at ambient temperature. The resulting mixture was stirred at 120° C. for 14 h. The volatile components were removed by evaporation and the resulting residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (1:1) to give 640 mg (1%) of the title compound as a pale yellow oil.

후처리

  1. customThe volatile components were removed by evaporation
  2. customthe resulting residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-f253e0b362cc4abca90dcacabee29f38
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705020B2

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