Triphenylphosphine → 1-(t-Butoxycarbonyl)-4-(1-(2-fur-2-ylmethoxy-ethyl)-1h-benzimidazole-2-carbonyl)piperidine

HRID 609785노트

반응식

HRID 609785 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[CH2:26][CH2:27][O:28][CH2:29][C:30]1[O:31][CH:32]=[CH:33][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CC(C)=O.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([C:16]2[N:17]([CH2:26][CH2:27][O:28][CH2:29][C:30]3[O:31][CH:32]=[CH:33][CH:34]=3)[C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10103270Fur-2-ylmethyl 2-hydroxyethyl etherHCID 183332351-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine

생성물 1

HCID 183334651-(t-Butoxycarbonyl)-4-(1-(2-fur-2-ylmethoxy-ethyl)-1h-benzimidazole-2-carbonyl)piperidine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21584124Propan-2-one--dichloromethane (1/1)용매2회

실험 절차

Combine ethyl 2-fur-2-ylmethoxyaceate (1.2 g, 6.5 mmol) and tetrahydrofuran (10 mL). Cool in an ice-bath. Add dropwise a solution of lithium aluminum hydride (8.0 mL, 1.0 M in THF, 8.0 mmol). After 2 hours, add water (0.3 mL), add 15% sodium hydroxide solution (0.3 mL), and add water (0.9 mL). Stir vigorously. After 15 minutes, filter the reaction mixture and dry the filtrate over Na2SO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 2% ethyl acetate/dichloromethane to give fur-2-ylmethyl 2-hydroxyethyl ether: Rf =0.22 (silica gel, 5% acetone/dichloromethane) Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine (1.71 g, 5.2 mmol), fur-2-ylmethyl 2-hydroxyethyl ether (0.74 g, 5.2 mmol), and triphenylphosphine (1.67 g, 6.4 mmol) in tetrahydrofuran (20 mL). Add diethyl azodicarboxylate (1.0 mL, 6.35 mmol). After 21 hours, evaporate the reaction mixture in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% acetone/dichloromethane to give 1-(t-butoxycarbonyl)-4-(1-(2-fur-2-ylmethoxy-ethyl)-1H-benzimidazole-2-carbonyl)piperidine: Rf =0.30 (silica gel, 5% acetone/dichloromethane).

후처리

  1. customevaporate the reaction mixture in vacuo
  2. customto give a residue

출처 및 근거

ORD 기록
ord-017f13f4d3ae4b45ad45a16432a5c221
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998439

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