Cyclohexanol → (2-Cyclohexyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester

HRID 2363391Notes

Reaction equation

C([O:5][C:6](=[O:18])[CH2:7][CH:8]([NH:11][C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])[CH2:9][OH:10])(C)(C)C.[CH:19]1(O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH2:15]([O:14][C:12](=[O:13])[NH:11][CH:8]1[CH2:7][C:6](=[O:5])[O:18][CH:9]1[O:10][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH:16]=[CH2:17]

Participants

Reactant 2

HCID 7966Cyclohexanol

HCID 542397063-Allyloxycarbonylamino-4-hydroxy-butyric acid tert-butyl ester

Product 1

HCID 54112717(2-Cyclohexyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl esterYield 85%

Procedure

Prepared from 3-allyloxycarbonylamino-4-hydroxy-butyric acid tert-butyl ester as described for 40 using cyclohexanol to afford the title compound as a mixture of diastereomers (pale yellow oil) (4.62 g, 85% yield). Flash column chromatography using hexanes/EtOAc (90/10 to 80/20) gave 394 mg (7% yield) of the syn diastereomer of the title compound. 1H NMR (500 MHz, CDCl3) 6.1.11-2.09 (m, 10H), 2.35-2.61 (dd, 1H), 2.72-2.98 (dd, 1H), 3.60-3.83 (m, 1H), 4.32-4.72 (m, 3H), 5.06-5.43 (m, 2H), 5.60 (d, 1H), 5.82-6.03 (m, 1H).

Sources & evidence

ORD record: ord-1eb4a0d3234449ae8cd9bc8bc83fed66
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691848B2

Reaction notes

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