N-benzyl-N-methyl-3-azabicyclo[3.2.1]octan-8-amine → tert-butyl (1S)-2-{8-[benzyl(methyl)amino]-3-azabicyclo-[3.2.1]oct-3-yl}-1-[(4-cyanophenoxy)methyl]ethylcarbamate

HRID 411549Notes

Reaction equation

[C:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C@@H:9]2[CH2:11][N:10]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:5][CH:4]=1)#[N:2].[CH2:21]([N:28]([CH3:37])[CH:29]1[CH:34]2[CH2:35][CH2:36][CH:30]1[CH2:31][NH:32][CH2:33]2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(O)C>[CH2:21]([N:28]([CH3:37])[CH:29]1[CH:34]2[CH2:35][CH2:36][CH:30]1[CH2:31][N:32]([CH2:11][C@H:9]([NH:10][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:20][CH:19]=1)[CH2:33]2)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tert-butyl (2S)-2-[(4-cyanophenoxy)methyl]-1-aziridinecarboxylate (see step (iii) above; 1.26 g, 4.6 mmol) and N-benzyl-N-methyl-3-azabicyclo[3.2.1]octan-8-amine (see step (vii) above; 1.05 g, 4.6 mmol) in IPA (15 mL) was stirred at 60° C. overnight. The solvent was evaporated and the residue purified by chromatography on silica gel, eluting with DCM:MeOH (20:1). This gave 1.8 g (78%) of the subtitle compound

Workup

customThe solvent was evaporated
customthe residue purified by chromatography on silica gel
washeluting with DCM:MeOH (20:1)

Sources & evidence

ORD record: ord-d576d169a82245cb96be257295757a49
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559162B2

Reaction notes

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