tert-Butanol → Methyl 2-(4-bromophenyl)-1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopropanecarboxylate

HRID 600308Notes

Reaction equation

P(N=[N+]=[N-])(=O)([O:9][C:10]1C=CC=CC=1)OC1C=CC=CC=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]2[CH2:29][C:28]2([C:33]([O:35][CH3:36])=[O:34])C(O)=O)=[CH:23][CH:22]=1.C([N:39](CC)CC)C.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>C1(C)C=CC=CC=1.O>[Br:20][C:21]1[CH:22]=[CH:23][C:24]([CH:27]2[CH2:29][C:28]2([NH:39][C:10]([O:48][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:9])[C:33]([O:35][CH3:36])=[O:34])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of diphenyl phosphorazidate (7.59 g), 2-(4-bromophenyl)-1-(methoxycarbonyl)cyclopropanecarboxylic acid (7.5 g), triethylamine (3.84 mL) in a mixture of toluene (300 mL) and tert-butanol (300 mL) was heated at 85° C. for 10 h. The mixture was diluted with water and the mixture was extracted with ether, washed with 5% aqueous citric acid, followed by saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. The crude product was purified by flash silica chromatography, eluting with 1:1 diethyl ether/isohexane. Pure fractions were evaporated to dryness to afford methyl 2-(4-bromophenyl)-1-(tert-butoxycarbonylamino)cyclo-propanecarboxylate (4.60 g) as a colourless solid.

Workup

extractionthe mixture was extracted with ether
washwashed with 5% aqueous citric acid
dry with materialdried over magnesium sulfate
customThe crude product was purified by flash silica chromatography
washeluting with 1:1 diethyl ether/isohexane
customPure fractions were evaporated to dryness

Sources & evidence

ORD record: ord-c515f630860b46eab44561d59f959bac
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902181B2

Reaction notes

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