HCID 66617615, compound → HCID 58944685, compound

HRID 222191Notes

Reaction equation

[Si:1]([O:18][CH2:19][C@H:20]1[C:24](=[O:25])[CH:23]=[CH:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][Li]>C(OCC)C>[Si:1]([O:18][CH2:19][C@H:20]1[C@@:24]([CH3:26])([OH:25])[CH:23]=[CH:22][CH2:21]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)cyclopent-2-en-1-one (250. mg, 0.713 mmol) in diethyl ether (10.0 mL) tinder an atmosphere of nitrogen was cooled to −40° C. and a 1.60 M solution of methyllithium in diethyl ether (0.579 mL, 0.926 mmol) was added slowly and the mixture was stirred at −40° C. for 3 h. TLC indicated complete conversion, and the reaction was quenched via addition of saturated aqueous ammonium chloride (5.00 mL), extracted with EtOAc (3×10.0 mL), dried over MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography eluting with a gradient of 0 to 50% EtOAc in hexanes afforded the title compound (190 mg, 73%). Stereochemistry of the product was confirmed using ROESY analysis. LC/MS: Rt=2.55 min, ES+ 367 (AA standard).

Workup

customthe reaction was quenched via addition of saturated aqueous ammonium chloride (5.00 mL)
extractionextracted with EtOAc (3×10.0 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
washSilica gel chromatography eluting with a gradient of 0 to 50% EtOAc in hexanes

Sources & evidence

ORD record: ord-c129206221d04b46abfdaa395c78db0e
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207177B2

Reaction notes

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