Potassium Carbonate → HCID 68519636, compound

HRID 1992359Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 4-bromomethylbenzonitrile (10 g, 0.054 mol), 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (11.5 g, 0.0439 mol; see WO 01/28992) and dry K2CO3 (21.2 g, 0.153 mol) in 200 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. The residue was purified by column chromatography over silica gel using 10% ethyl acetate in petroleum ether as eluent to yield (10 g) of the sub-title compound as colorless liquid.

Workup

filtrationThe reaction mixture was filtered through celite and filtrate
concentrationwas concentrated under reduced pressure
customThe residue was purified by column chromatography over silica gel using 10% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record: ord-ed0cab92055c478896a9b528659fb366
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648985B2

Reaction notes

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