Water → dimethyl{[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}amine

Participants

Reaction Conditions

Reaction Steps

(3S)—N,N-Dimethyl-5-oxo-4-(phenylmethyl)-3 morpholinecarboxamide (390 mg, 1.5 mmol) was dissolved in THF (20 mL) and the solution was cooled to 0° C. LiAlH4 (225 mg, 5.9 mmol) was added and the resulting mixture was refluxed overnight. Upon cooling to 0° C., water (1.4 mL) was added followed by 15% (w/w) NaOH (aq) (1.4 mL) and finally another portion of water (4.2 mL). Stirring for 30 min followed by filtration and concentration in vacuo yielded a crude mixture which was purified by RP-HPLC to provide dimethyl{[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}amine (510 mg, 41%). LCMS: (M+H)+: 235.2.

Provenance & Evidence