Pyridine → 4-(4-Iodo-phenyl)-4-(isobutoxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2180176

반응식

HRID 2180176 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:21][NH2:22])([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25].N1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)([CH2:21][NH:22][C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 62365Isobutyl chloroformateHCID 207794744-Aminomethyl-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 685338824-(4-Iodo-phenyl)-4-(isobutoxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester수율 62.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 4-aminomethyl-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.10 g, 0.24 mmol) in CH2Cl2 (1.0 mL) at room temperature under Ar was added isobutyl chloroformate(0.033 mL, 0.26 mmol, 1.1 eq.) followed by pyridine (0.25 mL). The mixture was stirred at room temperature for 16 h, diluted with EtOAc (5 mL), washed with saturated aqueous NaHCO3 (5 mL) and saturated brine (5 mL) and dried over Na2SO4. Filtration and rotary evaporation gave the crude 4-(4-iodo-phenyl)-4-(isobutoxycarbonylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil (0.075 g, 0.15 mmol, ˜62%). 1H NMR (300 MHz, CDCl3): δ 7.81 (d, 2H), 7.15 (d, 2H), 4.42 (br.t, 1H), 3.88 (d, 2H), 3.79 (m, 2H), 3.42 (br.m, 2H), 3.25 (br.t, 2H), 2.13 (br.m, 3H), 1.88 (m, 3H), 1.54 (s, 9H), 0.99 (d, 6H). MS: 417 (M−Boc).

후처리

  1. washwashed with saturated aqueous NaHCO3 (5 mL) and saturated brine (5 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and rotary evaporation

출처 및 근거

ORD 기록
ord-dbd9cfdfd3424431911ddd3a72c1b718
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887889B2

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