Methanol → (6R)-6-(Hydroxymethyl)morpholin-3-one

HRID 384718Notes

Reaction equation

HRID 384718 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][C@@H:7]([OH:10])[CH2:8][OH:9])=[O:4].CC(C)([O-])C.[K+].CO.O>C(O)(CC)(C)C>[OH:9][CH2:8][C@H:7]1[CH2:6][NH:5][C:3](=[O:4])[CH2:2][O:10]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 596135412-Chloro-N-[(2R)-2,3-dihydroxypropyl]acetamide

Product 1

HCID 34179996(6R)-6-(Hydroxymethyl)morpholin-3-oneYield 54.9%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent2×

Procedure

(R)-2-Chloro-N-(2,3-dihydroxypropyl)acetamide (1.31 g, 8.20 mmol) in tert-amyl alcohol (34 mL) was added dropwise over 2 h to a stirred solution of potassium tert-butoxide (2.30 g, 20.6 mmol) in tert-amyl alcohol (16 mL) at room temperature under nitrogen. After 1 hr, MeOH (8 mL) and water (0.5 mL) were added and the reaction mixture was stirred for an additional 20 min. The mixture was concentrated under vacuum and purified by flash column chromatography on silica gel, eluting with methanol/ethyl acetate (2/8) to give the title compound as a white solid (0.59 g, 54%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. custompurified by flash column chromatography on silica gel
  3. washeluting with methanol/ethyl acetate (2/8)

Sources & evidence

ORD record
ord-9d058689aeec4703b3abb3c41192bdb1
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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