2-Aminoadamantane → HCID 66884685, compound

HRID 72138

Reaction equation

HRID 72138 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH2:11])[CH2:8]2.C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1.CCN(C(C)C)C(C)C.[N:33]1([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:37]2([CH2:41][CH2:40][NH:39][CH2:38]2)[CH2:36][CH2:35][CH2:34]1>C(Cl)Cl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:17]([N:39]1[CH2:40][CH2:41][C:37]3([N:33]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:34][CH2:35][CH2:36]3)[CH2:38]1)=[O:18])[CH2:8]2

Participants

6

Reactant 4

HCID 253322-AminoadamantaneHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 426145731,7-Diaza-spiro(4.4)nonane-1-carboxylic acid tert-butyl ester

Product 1

HCID 66884685HCID 66884685, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of adamantan-2-ylamine (75 mg, 0.38 mmol), CDI (80 mg, 0.46 mmol), i-Pr2NEt (150 mg, 1.14 mmol) in CH2Cl2 (5 mL) was stirred at 0° C. for 1 h, and tert-butyl 1,7-diazaspiro[4.4]nonane-1-carboxylate (100 mg, 0.38 mmol) was added. The reaction mixture stirred at room temperature overnight. The solvent was removed under reduced pressure to give crude product which was purified by preparative TLC to afford tert-butyl 7-(2-adamantylcarbamoyl)-1,7-diazaspiro[4.4]nonane-1-carboxylate (136 mg, 89%). LC-MS Method 3, tR=4.24 min, m/z=404.1; 1H NMR (CDCl3) 1.39 (s, 9H), 1.48-1.52 (m, 4H), 1.62-1.71 (m, 5H), 1.71-1.81 (m, 10H), 1.81-1.88 (m, 3H), 1.89-2.01 (m, 1H), 2.93-3.12 (m, 1H), 3.21 (m, 1H), 3.28-3.49 (m, 2H), 3.55 (m, 1H), 3.68 (m, 1H), 3.88 (m, 1H), 4.46 (m, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give crude product which
  3. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-80deddb8ded445c392942df9ef9c08ce
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Linked notes

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