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

HRID 1499948ノート

反応式

HRID 1499948 の反応式
[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

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 866778635-(3-Acetyl-5-chloro-2-methoxy-6-methylphenyl)-1,3-oxazolidin-2-one

生成物 1

HCID 866778645-[3-Chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]-1,3-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  1. custompurified on preparative LCMS

出典と根拠

ORDレコード
ord-7ee39d63e0d64523a98a4d4772a366fd
出典データセット
uspto-grants-2015_12
特許番号
US09199982B2

反応ノート

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