Water → HCID 58092775, compound

HRID 1430131Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]([Cl:21])([Cl:20])[C@@H:11]1[N:15]2[CH2:16][CH2:17][CH2:18][C@H:14]2[C:13](=[O:19])[O:12]1.[CH3:22][N+:23]([CH3:25])=[CH2:24].[I-].O>C1COCC1>[CH3:22][N:23]([CH2:25][C@@:14]12[CH2:18][CH2:17][CH2:16][N:15]1[C@@H:11]([C:10]([Cl:9])([Cl:20])[Cl:21])[O:12][C:13]2=[O:19])[CH3:24]

Participants

Conditions

Temperature: -78 °C

Procedure

A 1M of solution of lithium diisopropylamide in a 3:5 mixture of hexanes/THF (8.25 ml) is added dropwise to (3R,7aS)-3-trichloromethyl-tetrahydro-pyrrolo[1,2-c]oxazol-1-one (1.51 g, prepared as described by Wang and Germanas Synlett 1999, 33-36.) in THF (5 ml) at −78° C. After stirring 30 minutes at −78° C. Eschenmoser's salt (2.78 g) is added. The reaction mixture is then allowed to warm to −40° C. with vigorous stirring over 1 hour and maintained for 2 hours at −40° C. Water is then added and the aqueous layer extracted with dichloromethane, the combined organic layers dried over sodium sulphate and evaporated. The residue is then purified by mormal phase chromatography eluting with a gradient from dichloromethane to 20% ethyl acetate in dichloromethane to give the title compound as a pale yellow oil.

Workup

temperatureto warm to −40° C.
stirringwith vigorous stirring over 1 hour
temperaturemaintained for 2 hours at −40° C
extractionthe aqueous layer extracted with dichloromethane
dry with materialthe combined organic layers dried over sodium sulphate
customevaporated
customThe residue is then purified by mormal phase chromatography
washeluting with a gradient from dichloromethane to 20% ethyl acetate in dichloromethane

Sources & evidence

ORD record: ord-0cfce42dbb784da99db5f426c8c47057
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940771B2

Reaction notes

Loading…