Methylamine → Benzyl 1-(methylamino)-3-(1-methylcyclohexyl)propan-2-ylcarbamate

HRID 451789Notes

Reaction equation

CS(O[CH2:6][CH:7]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:8][C:9]1([CH3:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=O)=O.[CH3:27][NH2:28]>C1COCC1.CCO>[CH3:27][NH:28][CH2:6][CH:7]([NH:16][C:17](=[O:18])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:8][C:9]1([CH3:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate in 16 mL of THF, and 10 mL of 33% wt. methylamine in EtOH was heated at 70° C. for 3 h. After cooling to rt, the reaction mixture was evaporated under reduced pressure. The crude benzyl 1-(methylamino)-3-(1-methylcyclohexyl)propan-2-ylcarbamate was used directly in the next step without further purification. MS ESI +ve m/z 319 (M+H).

Workup

temperatureAfter cooling to rt
customthe reaction mixture was evaporated under reduced pressure
customThe crude benzyl 1-(methylamino)-3-(1-methylcyclohexyl)propan-2-ylcarbamate was used directly in the next step without further purification

Sources & evidence

ORD record: ord-8c932ee858c047c6af60dedc3a488867
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487108B2

Reaction notes

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