Sodium borohydride → 5-[3-Chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]-1,3-oxazolidin-2-one

HRID 1499948Notes

Reaction equation

[C:1]([C:4]1[C:5]([O:18][CH3:19])=[C:6]([CH:12]2[O:16][C:15](=[O:17])[NH:14][CH2:13]2)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[Cl:10][C:8]1[C:7]([CH3:11])=[C:6]([CH:12]2[O:16][C:15](=[O:17])[NH:14][CH2:13]2)[C:5]([O:18][CH3:19])=[C:4]([CH:1]([OH:3])[CH3:2])[CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(3-acetyl-5-chloro-2-methoxy-6-methylphenyl)-1,3-oxazolidin-2-one (21 mg, 0.072 mmol) (single enantiomer from step 1) in methanol (1 mL) was added sodium tetrahydroborate (5.5 mg, 0.14 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour. It was diluted with methanol and purified on preparative LCMS using pH 10 buffer to give the desired compound as a racemic mixture of two diastereomers, 17 mg, 83%. LCMS calculated for C13H15ClNO3 (M-OH)+: m/z=268.1; found: 268.1.

Workup

custompurified on preparative LCMS

Sources & evidence

ORD record: ord-7ee39d63e0d64523a98a4d4772a366fd
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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