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

HRID 1423117ノート

反応式

HRID 1423117 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 (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 the title compound as a foam (60 mg, 69%) 1H NMR (CDCl3) 7.35-7.22 (m, 5H), 6.78 (d, J=8.8, 1H), 6.49 (br s, 1H), 6.40 (br d, J=7.5, 1H), 4.73-4.70 (m, 1H), 4.27-4.13 (m, 2H), 3.93 (br d, J=12.5, 1H), 3.79 (s, 3H), 3.43-3.00 (m, 7H), 2.75-2.67 (m, 2H), 1.96-1.91 (m, 2H), 1.90-1.79 (m, 3H), 1.64-1.59 (m, 2H), 1.04 (t, J=7.2, 3H). LC/MS (Method A) 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-f37bd2ddb2bc43dba48e23995fafe303
出典データセット
uspto-grants-2015_01
特許番号
US08927546B2

反応ノート

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