Methylamine → Benzyl 1-(bicyclo[2.2.2]octan-1-yl)-3-(methylamino)propan-2-ylcarbamate

HRID 451798Notes

Reaction equation

CS(O[CH2:6][CH:7]([NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:8][C:9]12[CH2:16][CH2:15][CH:12]([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)(=O)=O.[NH2:28][CH3:29]>CO>[C:9]12([CH2:8][CH:7]([NH:17][C:18](=[O:19])[O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:6][NH:28][CH3:29])[CH2:16][CH2:15][CH:12]([CH2:13][CH2:14]1)[CH2:11][CH2:10]2

Participants

Conditions

Temperature: 35 °C

Procedure

2-(benzyloxycarbonylamino)-3-(bicyclo[2.2.2]octan-1-yl)propyl methanesulfonate (830 mg, 2.1 mmol) was dissolved in 15 mL of NH2Me in MeOH and stirred at 30-40° C. overnight. The mixture was concentrated to give benzyl 1-(bicyclo[2.2.2]octan-1-yl)-3-(methylamino)propan-2-ylcarbamate (1.0 g, crude) as an oil, which was used in the next step without further purification. MS ESI +ve m/z 331 (M+H).

Workup

concentrationThe mixture was concentrated

Sources & evidence

ORD record: ord-3c61f87e1cd34585b2a77984a0b00d05
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487108B2

Reaction notes

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