Benzoyl chloride → [[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-cyclopentyl-methyl] benzoate

HRID 60704Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[O:6][C@H:5]2[O:7][C@H:8]([CH:10]([CH:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[OH:11])[CH2:9][C@H:4]2[O:3]1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:18]([O:11][CH:10]([C@H:8]1[O:7][C@@H:5]2[O:6][C:2]([CH3:17])([CH3:1])[O:3][C@@H:4]2[CH2:9]1)[CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of [(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-cyclopentyl-methanol (compound 11a, 1.2 g, 5.0 mmol), TEA (3.2 g, 31.2 mmol) and DMAP (100 mg) in DCM (50 mL) was added benzoyl chloride (1.4 g, 10.0 mmol) slowly at 0° C. The mixture was stirred at 25° C. for 4 hours and then quenched by saturated NaHCO3 solution. The reaction mixture was extracted with EtOAc (100 mL) twice. The organic layers were combined, washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:20 to 1:5 EtOAc in petroleum ether) to afford 1.4 g of [[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-cyclopentyl-methyl] benzoate (compound 11b) as a colourless oil.

Workup

customquenched by saturated NaHCO3 solution
extractionThe reaction mixture was extracted with EtOAc (100 mL) twice
washwashed with brine (50 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel (eluting with 1:20 to 1:5 EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-b8fb6689a074479196b755c2f9e56f48
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09441008B2

Reaction notes

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