Lithium borohydride → (R)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

HRID 1781343Notes

Reaction equation

HRID 1781343 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=O.[BH4-].[Li+]>CCOCC>[CH3:11][C:7]1([CH3:10])[N:6]([C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C@H:5]([CH2:3][OH:2])[CH2:9][O:8]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 53934458(S)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinecarboxylic Acid Methyl Ester

Product 1

HCID 54137581(R)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 8a (296 mg, 1.09 mmol) in dry ether (1 mL) is treated with lithium borohydride (2M solution in THF, 0.55 mL, 1.09 meq) under an argon atmosphere. The mixture is stirred for 3 hr 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 δ 0.88 (m, 3 H), 1.30 (m, 6 H), 1.54 (s, 3 H), 1.62 (s, 3 H), 2.35 (m, 2 H), 3.30-4.40 (complex m, 6 H); MS (HR-E1) m/z 243.1837 (M calcd. for C13H25NO3 243.1840); [α]D26 =-5±1 (CHCl3).

Workup

  1. customquenched with methanol
  2. customThe volatiles are removed

Sources & evidence

ORD record
ord-6be7cdeeabcd409597ffca3d172897d1
Source dataset
uspto-grants-1997_05
Patent number
US05633280

Reaction notes

Loading…