tert-Butyl N-allyl-N-[2-hydroxyimino-2-phenyl-ethyl]carbamate → tert-Butyl 6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate

HRID 338095Notes

Reaction equation

[CH2:1]([N:4]([CH2:12][C:13](=[N:20][OH:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3]>C1(C)C(C)=CC=CC=1>[C:7]([O:6][C:5]([N:4]1[CH2:1][CH:2]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([NH:20][O:21][CH2:3]2)[CH2:12]1)=[O:11])([CH3:10])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 130 °C

Procedure

A solution of tert-butyl N-allyl-N-[-2-hydroxyimino-2-phenyl-ethyl]carbamate as a mixture of E and Z isomers (3.2 g, 10.9 mmol) in xylene (100 mL) is stirred at 100° C. for 2 hours, 130° C. for 6 hours, 100° C. for 12 hours and 130° C. for 2 hours. The cooled reaction is concentrated under reduced pressure to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1) to give the title compound (1.5 g, 48%). ES/MS (m/e): 291 (M+H).

Workup

customThe cooled reaction
concentrationis concentrated under reduced pressure
customto give a residue
customThe residue is purified by silica gel flash chromatography
washeluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1)

Sources & evidence

ORD record: ord-cfee2418fc9144aba2ea4f1dbba4b102
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889856B2

Reaction notes

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