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

HRID 379462ノート

反応式

HRID 379462 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21584124Propan-2-one--dichloromethane (1/1)溶媒2 回

実験手順

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, 1.0M 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 vacua 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 nmol), 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).

後処理

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

出典と根拠

ORDレコード
ord-6ec932ba616941f28cdd6a0fea9ce53c
出典データセット
uspto-grants-2001_10
特許番号
US06297259B1

反応ノート

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