Hydrochloric Acid → HCID 57518642, compound

HRID 1258123Notes

Reaction equation

HRID 1258123 reaction equation
[CH3:1][C@@:2]1([NH:17]C(=O)OC(C)(C)C)[CH2:6][CH2:5][C@H:4]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])[C:3]1([CH3:16])[CH3:15].[ClH:25]>C(OCC)(=O)C>[ClH:25].[NH2:17][C@:2]1([CH3:1])[CH2:6][CH2:5][C@H:4]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])[C:3]1([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57518641HCID 57518641, compound

Product 1

HCID 57518642HCID 57518642, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of intermediate 6 (0.27 g. 1.0 mmol), 1,1′-Carbonyldiimidazole (0.19 g, 1.2 mmol) and piperidine (0.10 g, 1 mmol) in dichloromethane was stirred at room temperature for 8 h. The reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous Na2SO4 and concentrated. Crude material was purified by column chromatography to obtain tert-butyl (1R,3S)-1,2,2-trimethyl-3-(piperidine-1-carbonyl)cyclopentylcarbamate. To the solution of tert-butyl (1R,3S)-1,2,2-trimethyl-3-(piperidine-1-carbonyl)cyclopentylcarbamate in ethyl acetate was added hydrochloride solution in ethylacetate and stirred for 2 h to afford ((1S,3R)-3-amino-2,2,3-trimethylcyclopentyl)(piperidin-1-yl)methanone hydrochloride. 1H NMR (400 MHz, D2O) δ ppm: 0.98 (s, 3H), 1.11 (s, 3H), 1.31 (s, 3H), 1.54-1.60 (m, 6H), 1.94-2.20 (m, 4H), 3.47-3.48 (m, 1H), 3.54-3.57 (m, 2H), 3.65-3.66 (m, 2H). m/z (M+H): 239.2.

Sources & evidence

ORD record
ord-483ce260e0314b19bb966a907e2ffdfa
Source dataset
uspto-grants-2013_06
Patent number
US08466145B2

Reaction notes

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