Cyclopentanemethanol → (2-Cyclopentylmethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester

HRID 900598Notes

Reaction equation

HRID 900598 reaction equation
C(OC(=O)CC(NC(OCC=C)=O)CO)(C)(C)C.[CH2:19]([O:22][C:23](=[O:40])[NH:24][CH:25]1[CH2:29][C:28](=[O:30])[O:27][CH:26]1[O:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=CC=1)[CH:20]=[CH2:21].C1(CO)CCCC1>>[CH2:19]([O:22][C:23](=[O:40])[NH:24][CH:25]1[CH2:29][C:28](=[O:30])[O:27][CH:26]1[O:31][CH2:32][CH:33]1[CH2:34][CH2:39][CH2:38][CH2:37]1)[CH:20]=[CH2:21]

Participants

4

Reactant 3

HCID 77195CyclopentanemethanolHCID 18465651(5-Oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-carbamic acid allyl esterHCID 542397063-Allyloxycarbonylamino-4-hydroxy-butyric acid tert-butyl ester

Product 1

HCID 54338860(2-Cyclopentylmethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester

Procedure

Prepared from 3-allyloxycarbonylamino-4-hydroxy-butyric acid tert-butyl ester as described for compound 40 using cyclopentylmethanol (6.5 mL, 60 mmol) to afford 2.98 grams (52% total yield) of the title compound as a mixture of epimers. Purification provided 0.97 grams (17% yield) of the 4(S), 5(R) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.19 (m, 2H), 1.54 (m, 4H), 1.71 (m, 2H), 2.16 (m, 1H), 2.44 (dd, J=17.2, 10.4 Hz, 1H), 2.82 (dd, J=17.2, 8.4 Hz, 1H), 3.44 (dd, J=9.3, 7.2 Hz, 1H), 3.71 (dd, J=9.3, 7.2 Hz, 1H), 4.57 (m, 3H), 5.32 (m, 3H), 5.41 (d, J=5.2 Hz, 1H), 5.91 (ddt, J=17.1, 10.4, 5 Hz, 1H) ppm. LC-MS. (ES+): m/e=284.

Workup

  1. customto afford

Sources & evidence

ORD record
ord-172f5f85971346c2a10577e98ec9377d
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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