Diiodomethane → HCID 86731612, compound
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
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
To a solution of (7aR)-3-(trichloromethyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one (D1) (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 (D2) 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-68772746719846e8959ea75a9d452883
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120824B2
Reaction notes
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