Ethyl Acetate → HCID 178451153, compound

HRID 928126Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li+].CCC[CH2-].[C:11]([C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])[CH2:16][CH2:15]1)(=[O:13])[CH3:12].CCOC(C)=O>C1COCC1.O>[OH:13][C:11]([C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])[CH2:16][CH2:15]1)([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

Thiazole (100 mg, 1.175 mmol) was dissolved in THF (11 mL) and cooled to a temperature of −78° C. N-butyllithium (2 M in hexanes, 0.587 mL, 1.175 mmol) was added and the mixture was allowed to stir for 30 minutes at −78° C. A solution of trans-butyl 4-acetylcyclohexanecarboxylate (319 mg, 1.410 mmol) in THF (1 mL) was then added to the mixture, and the combined solution was allowed to stir for 1 hour at −78° C. The reaction was diluted with water, warmed to 23° C., and transferred to a separatory funnel containing EtOAc. The layers were separated and the organic layer was washed with water, dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel to afford butyl trans-4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexanecarboxylate. MS ESI calc'd. for C16H26NO3S [M+H]+ 312. found 312.

Workup

stirringto stir for 1 hour at −78° C
temperaturewarmed to 23° C.
customtransferred to a separatory funnel
customThe layers were separated
washthe organic layer was washed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-9e86647da2784b6792a1b39b42de31f7
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290490B2

Reaction notes

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