Citric Acid → (4-Benzylmorpholin-2-yl)methanol

Temperature

2.5 °C

To a solution of 4-benzylmorpholine-2-carboxylic acid (5 g, 22.6 mmol) and triethylamine (3.35 mL, 24 mmol) in THF (100 mL) at −10° C. in a flask equipped with a condenser was added ethyl carbonochloridate (2.5 g, 23 mmol) dropwise and the mixture was stirred at −10° C. to −5° C. for 20 min. Sodium borohydride (2.27 g, 60 mmol) was added followed by methanol (25 mL) from the top of the condenser at such rate to maintain the temperature between 0-5° C. The reaction mixture was allowed to warm to room temperature, acidified to pH 5 with the addition of 10% aqueous citric acid, and concentrated under reduced pressure. The residue was dissolved in EtOAc, washed with water, brine, and dried with MgSO4. Purification of the residue by column chromatography (SiO2, eluted with EtOAc) afforded 3 g of the title compound. MS (DCI/NH3) m/z 208 (M+H)+.

1. temperatureto warm to room temperature
2. concentrationconcentrated under reduced pressure
3. dissolutionThe residue was dissolved in EtOAc
4. washwashed with water, brine
5. dry with materialdried with MgSO4
6. customPurification of the residue
7. washby column chromatography (SiO2, eluted with EtOAc)

ORD record

ord-37db046a350a441399b0ff68a327bdd5

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846730B2