Methanol → (S)-6-(Hydroxymethyl)morpholin-3-one
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]1Participants
6
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
- concentrationThe mixture was concentrated under vacuum
- custompurified by flash column chromatography on silica gel
- washeluting with methanol/ethyl acetate (2/8)
Sources & evidence
- ORD record
- ord-11bd976c6e7c45ee9bad9c13f57e501a
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367658B2
Reaction notes
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