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

HRID 556873Notes

Reaction equation

HRID 556873 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 11378718(S)-2-Chloro-N-(2,3-dihydroxypropyl)acetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 11446350(S)-6-(Hydroxymethyl)morpholin-3-oneYield 45%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent2×

Procedure

(S)-2-Chloro-N-(2,3-dihydroxypropyl)acetamide (4.77 g, 28.45 mmol) in tert-amyl alcohol (75 mL) was added over 2 h to a stirred solution of potassium tert-butoxide (3.59 g, 21.4 mmol) in tert-amyl alcohol (25 mL) at room temperature under nitrogen. After 1 hr, methanol (12 mL) and water (0.7 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 (1.26 g, 45%).

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-c4ccb254c66c44bd94aca99f65d1f2d7
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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