2-Aminoadamantane hydrochloride → N-(2-adamantyl)-3-cyclopentyl-3-oxo-propanamide

HRID 1160550Notes

Reaction equation

Cl.[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH2:12])[CH2:9]2.[CH:13]1([C:18]([CH:20]2C(=O)OC(C)(C)[O:22][C:21]2=O)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(C(C)C)C(C)C)C>C1(C)C=CC=CC=1.CCOC(C)=O>[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH:12][C:21](=[O:22])[CH2:20][C:18]([CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:19])[CH2:9]2

Participants

Conditions

Temperature: 110 °C

Procedure

2-Adamantanamine hydrochloride (1.641 g, 8.74 mmol) was added to 5-(cyclopentanecarbonyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (Intermediate#77), (2.1 g, 8.74 mmol) and N-Ethyldiisopropylamine (1.512 mL, 8.74 mmol) in toluene (30 mL). The resulting suspension was stirred at 110° C. for 2 hours. The reaction mixture was diluted with EtOAc (100 mL), and washed sequentially with 2M HCl (20 mL), and water (2×50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford N-(2-adamantyl)-3-cyclopentyl-3-oxo-propanamide (1.030 g, 40.7%) as a brown oil which crystallised on standing.

Workup

washwashed sequentially with 2M HCl (20 mL), and water (2×50 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated
customto afford crude product
customThe crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane
customPure fractions were evaporated to dryness

Sources & evidence

ORD record: ord-13e14de7f8d14e099e1028266ecedb38
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816391B2

Reaction notes

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