Potassium Carbonate → HCID 68519636, compound

HRID 2078426Notes

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-diazabicyclo[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 μL of dry acetonitrile was stirred at 60° C. overnight under a N2 atmosphere. The reaction mixture was filtered through Celite® and the 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 colourless liquid.

Workup

filtrationThe reaction mixture was filtered through Celite®
concentrationthe filtrate was 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-1830a6370e584a149d10c5098d56919b
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928225B2

Reaction notes

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