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

HRID 1499944Notes

Reaction equation

HRID 1499944 reaction equation
[C:1]([C:4]1[C:5]([O:19][CH3:20])=[C:6]([CH:12]2[CH2:17][NH:16][C:15](=[O:18])[CH2:14][O: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[CH2:17][NH:16][C:15](=[O:18])[CH2:14][O:13]2)[C:5]([O:19][CH3:20])=[C:4]([CH:1]([OH:3])[CH3:2])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866778596-(3-Acetyl-5-chloro-2-methoxy-6-methylphenyl)morpholin-3-one

Product 1

HCID 866778606-[3-Chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]morpholin-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-(3-acetyl-5-chloro-2-methoxy-6-methylphenyl)morpholin-3-one (27 mg, 0.090 mmol) (single enantiomer from step 4) in methanol (2 mL) was added sodium tetrahydroborate (6.8 mg, 0.18 mmol) at 0° C. and stirred for 1 hour. Purification by preparative LCMS (pH 10) gave the desired compound as a racemic mixture of two diastereomers, 20 mg, 76%. LCMS calculated for C14H17ClNO3 (M-OH)+: m/z=282.1; found: 282.1.

Workup

  1. customPurification by preparative LCMS (pH 10)

Sources & evidence

ORD record
ord-9da582a1280e4c709ebdae64722db906
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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