Acetic Acid → (3aR,4R,5R,6aS)-4-((R)-3-Hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol

HRID 584886Notes

Reaction equation

[OH:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][CH:7]([OH:9])[CH2:8][C@@H:4]2[C@H:3]1[CH2:11][CH2:12][C@@H:13]([O:22]C1CCCCO1)[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C1COCC1.[OH-].[K+]>O>[OH:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][CH:7]([OH:9])[CH2:8][C@@H:4]2[C@H:3]1[CH2:11][CH2:12][C@@H:13]([OH:22])[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of compound [11a] (0.55 g), acetic acid (2 ml), THF (2 mL) and water (2 mL) was stirred at 40-50° C. for 4 hours (TLC monitoring). The mixture was basified with 1 N aq. potassium hydroxide to pH 10-11 and the product was extracted with dichloromethane (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (elution with gradient ethyl acetate/hexane from 1:2 to 3:1 v/v) to give 0.18 g (43%) of the compound [11b] as a colorless oil. 1H NMR (CD3OD) is compatible with literature data.

Workup

extractionthe product was extracted with dichloromethane (3×20 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel (elution with gradient ethyl acetate/hexane from 1:2 to 3:1 v/v)

Sources & evidence

ORD record: ord-d06e9afb6d9947949531e0f30b3afa13
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06927300B2

Reaction notes

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