1-Adamantanecarboxylic acid → N-(3-hydroxybutyl)adamantane-1-carboxamide

HRID 75164

反応式

HRID 75164 の反応式
[C:1]12([C:11]([OH:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:14][CH2:15][CH2:16][CH:17]([OH:19])[CH3:18].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[OH:19][CH:17]([CH3:18])[CH2:16][CH2:15][NH:14][C:11]([C:1]12[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2)=[O:13]

参加物

7

反応物 5

HCID 132351-Adamantanecarboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1702542-Butanol, 4-amino-

生成物 1

HCID 59437164N-(3-hydroxybutyl)adamantane-1-carboxamide収率 30.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Adamantane-1-carboxylic acid (404 mg, 2.24 mmol), 4-amino-butan-2-ol (200 mg, 2.24 mmol), EDCI (885 mg, 4.48 mmol) and HOBt (605 mg, 4.48 mmol) were dissolved in anhydrous CH2Cl2. DIEA (1.444 g, 11.2 mmol) was added to the above mixture at 0° C. under nitrogen. The mixture was stirred overnight and concentrated to give a residue, which was purified by preparative TLC to provide N-(3-hydroxybutyl)adamantane-1-carboxamide (170 mg, 30%). 1H NMR (MeOD, 400 MHz): δ=1.20 (d, 3H), 1.66˜2.04 (m, 17H), 2.87 (m, 2H), 3.79(m, 1H).

後処理

  1. concentrationconcentrated
  2. customto give a residue, which
  3. customwas purified by preparative TLC

出典と根拠

ORDレコード
ord-0bbed32b62c949fca5a7680e4c4e397f
出典データセット
uspto-grants-2014_09
特許番号
US08835426B2

関連ノート

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