Potassium Carbonate → {3-[7-(4-Cyano-benzyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-propyl}-carbamic acid tert-butyl ester

HRID 1992360Notes

Reaction equation

Cl.[CH:2]12[O:10][CH:6]([CH2:7][NH:8][CH2:9]1)[CH2:5][N:4]([CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[CH2:3]2.[C:20]([O:24][C:25](=[O:31])[NH:26][CH2:27][CH2:28][CH2:29]Br)([CH3:23])([CH3:22])[CH3:21].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:20]([O:24][C:25](=[O:31])[NH:26][CH2:27][CH2:28][CH2:29][N:8]1[CH2:9][CH:2]2[O:10][CH:6]([CH2:5][N:4]([CH2:11][C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[CH2:3]2)[CH2:7]1)([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 4-(9-Oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl-methyl)-benzonitrile hydrochloride (6.8 g, 0.021 mol; from step (ii) above), (3-Bromopropyl)-carbamic acid tert-butyl ester (3.93 g, 0.017 mol) and dry K2CO3 (8.24 g, 0.059 mol) in 27 ml of dry acetonitrile was stirred at 60° C. overnight under N2 atmosphere. The reaction mixture was filtered through celite and filtrate was concentrated under reduced pressure to give (7.5 g) of the sub-title compound as pale a liquid.

Workup

filtrationThe reaction mixture was filtered through celite and filtrate
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-222e9850e0504135a7de85d18e446f66
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648985B2

Reaction notes

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