반응 #80529

반응 방정식

8a

(S)-2,2-Dimethyl-3-(1-oxoheptyl]-4-oxazolidinecarboxylic Acid Methyl Ester

lithium borohydride

→

alcohol

(R)-2,2-Dimethyl-3-(1-oxoheptyl]-4-oxazolidinemethanol

용매

ether

ether

반응 조건

후처리

1. 1
   기타quenched with methanol
2. 2
   기타The volatiles are removed

실험 절차

A solution of 8a (296 mg, 1.09 mmol) in dry ether (1 mL) is treated with lithium borohydride (2 M solution in THF, 0.55 mL, 1.09 meq) under an argon atmosphere. The mixture is stirred for 3 h at reflux and 18 h at room temperature. The resulting mixture is diluted with ether and quenched with methanol. The volatiles are removed and the residue is taken up in EtOAc/H2O. Workup provides the crude alcohol which is purified by chromatography (2:1 hexane/EtOAc): NMR δ0.88 (m, 3H), 1.30 (m, 6H), 1.54 (s, 3H), 1.62 (s, 3H), 2.35 (m, 2H), 3.30-4.40 (complex m, 6H); MS (HR-E1) m/z 243.1837 (M calcd. for C13H25NO3 243.1840); [α]D26 =-5±1 (CHCl3).

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