Ethyl isocyanate → (S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine-1-carboxylic acid ethylamide

HRID 1171905ノート

反応式

HRID 1171905 の反応式
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([N:30]=[C:31]=[O:32])[CH3:29]>C(Cl)Cl>[CH2:28]([NH:30][C:31]([N:13]1[CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9][C@@H:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:32])[CH3:29]

参加物

4

反応物 2

HCID 8022Ethyl isocyanateHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

生成物 1

HCID 23627685(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine-1-carboxylic acid ethylamide収率 69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (73 mg, 0.2 mmol) in CH2Cl2 (0.5 mL) at 0° C. was treated with ethyl isocyanate (19 μL, 0.24 mmol) and stirred for 1 h, then evaporated and the residue purified by silica gel flash chromatography with 50% then 75% EtOAc/hexane as eluant to afford product as a foam (60 mg, 69%) 1H NMR (CDCl3) 1.04 (t, J=7.2, 3H), 1.59-1.64 (m, 2H), 1.79-1.90 (m, 3H), 1.91-1.96 (m, 2H), 2.67-2.75 (m, 2H), 3.00-3.43 (m, 7H), 3.79 (s, 3H), 3.93 (br d, J=12.5, 1H), 4.13-4.27 (m, 2H), 4.70-4.73 (m, 1H), 6.40 (br d, J=7.5, 1H), 6.49 (br s, 1H), 6.78 (d, J=8.8, 1H), 7.22-7.35 (m, 5H). LC/MS 6.86 min, [M+1]+ 438.

後処理

  1. customevaporated
  2. customthe residue purified by silica gel flash chromatography with 50%

出典と根拠

ORDレコード
ord-c6d8770a06154e7d891362b0a06be6aa
出典データセット
uspto-grants-2010_11
特許番号
US07829713B2

反応ノート

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