Diiodomethane → 7a-methyl-3-(trichloromethyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one

HRID 712817Notes

Reaction equation

[Cl:1][C:2]([Cl:13])([Cl:12])[CH:3]1[N:7]2[CH2:8][CH2:9][CH2:10][C@@H:6]2[C:5](=[O:11])[O:4]1.[Li+].[CH3:15]C([N-]C(C)C)C.C1COCC1.CCCCCCC.ICI>C1COCC1>[CH3:15][C:6]12[CH2:10][CH2:9][CH2:8][N:7]1[CH:3]([C:2]([Cl:1])([Cl:12])[Cl:13])[O:4][C:5]2=[O:11]

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of (7aR)-3-(trichloromethyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one (D48) (0.2 g, 0.82 mol) in THF (10 ml) cooled at −78° C. LDA 2M sol in THF/heptane (0.58 ml, 1.17 mol) was added and the mixture stirred 30 min. Diiodomethane (0.185 ml, 2.97 mol) was added and the temperature was allowed to warm to −40° C. over a period of 2 hrs then left at this temperature for an additional hour. The resulting mixture was partitioned between DCM and H2O. The aqueous phase was extracted with DCM (2×10 ml); the organic phases were collected, dried over Na2SO4 and evaporated in vacuo. The residue was purified by SPE-Si cartridge (25 g) eluting with DCM. Collected fractions after solvent evaporation afforded title compound (D49) in mixture (4:1) with starting material (110 mg).

Workup

additionwas added
waitthen left at this temperature for an additional hour
customThe resulting mixture was partitioned between DCM and H2O
extractionThe aqueous phase was extracted with DCM (2×10 ml)
customthe organic phases were collected
dry with materialdried over Na2SO4
customevaporated in vacuo
customThe residue was purified by SPE-Si cartridge (25 g)
washeluting with DCM
customCollected fractions after solvent evaporation

Sources & evidence

ORD record: ord-2a7302d9829f424598f76bd10564b77a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181279B2

Reaction notes

Loading…