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

HRID 75164

Reaction equation

HRID 75164 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-0bbed32b62c949fca5a7680e4c4e397f
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Linked notes

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