tert-Butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-ethylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate → 4-(4-Amino-3-ethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2272428노트

반응식

HRID 2272428 반응식
C(OC([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=2)=[CH:14][C:13]=1[CH2:31][CH3:32])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:22][CH2:23]2)=[CH:14][C:13]=1[CH2:31][CH3:32]

참가 물질

4

반응물 1

HCID 71232505tert-Butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-ethylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

생성물 1

HCID 866758434-(4-Amino-3-ethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester수율 61%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매2회

실험 절차

tert-Butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-ethylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (I39) (0.500 g, 1.14 mmol) was dissolved in ethanol (20 mL), and a slurry of 10% Pd/C (0.25 g) in ethanol (2 mL) was added. The mixture was stirred under hydrogen for 18 hours, then filtered through celite, washing the celite with ethanol (30 mL). The combined filtrates were evaporated, and chromatography (12 g silica cartridge, 0-80% ethyl acetate/petroleum benzine 40-60° C.) gave the title compound (I40) (0.212 g, 61% yield) as a pink syrup; 1H NMR (400 MHz, CDCl3) δ 6.90 (d, J=2.0 Hz, 1H), 6.87 (dd, J=8.0, 2.1 Hz, 1H), 6.63 (d, J=8.0 Hz, 1H), 4.21 (s, 2H), 3.55 (s, 2H), 2.78 (t, J=12.2 Hz, 2H), 2.59-2.46 (m, 3H), 1.78 (d, J=13.2 Hz, 2H), 1.66-1.53 (m, overlaps with water), 1.48 (s, 9H), 1.25 (t, J=7.5 Hz, 3H). LCMS Method C: rt 5.33 min; m/z 249.2 [M-tBu+2H]+, 205.2 [M-Boc+2H]+.

후처리

  1. filtrationfiltered through celite
  2. washwashing the celite with ethanol (30 mL)
  3. customThe combined filtrates were evaporated

출처 및 근거

ORD 기록
ord-a3c7599c2c974a30864dca474b7e6cd7
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120761B2

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