Isobutyronitrile → HCID 89827711, compound

HRID 522700Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[C:13](#[N:17])[CH:14]([CH3:16])[CH3:15].Br[CH2:19][CH2:20][NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1.O>[C:13]([C:14]([CH3:16])([CH3:15])[CH2:19][CH2:20][NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)#[N:17]

Participants

Conditions

Temperature: -78 °C

Procedure

Treat a −78° C. solution of diisopropylamine (35 g, 0.346 mol) in THF (300 mL), under N2, dropwise with a solution of n-butyllithium (2.5 M, 127 mL, 0.317 mol), warm to −30° C. for 0.5 h, re-cool to −78° C. and treat dropwise with a solution of isobutyronitrile (19.9 g, 0.288 mol) in THF (100 mL). Stir the mixture at −78° C. for 0.5 h, treat with a solution of benzyl (2-bromoethyl)carbamate (74 g, 0.288 mol) in THF (100 mL), stir at −78° C. for 1 h, then warm to RT and stir overnight. Treat the mixture with H2O, separate the layers, extract the aqueous layer with EtOAc, wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Petroleum ether) to afford the title compound (15 g, 21% yield). MS (m/z): 247.2 (M+1).

Workup

stirringstir at −78° C. for 1 h
temperaturewarm to RT
stirringstir overnight
customseparate the layers
extractionextract the aqueous layer with EtOAc
washwash the combined organics with brine
dry with materialdry over Na2SO4
concentrationconcentrate to dryness
custompurify via silica gel chromatography (EtOAc/Petroleum ether)

Sources & evidence

ORD record: ord-803d0950c11840bbb124259da76804ca
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334267B2

Reaction notes

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