Lithium Hydroxide → 2-(3-Methoxyphenyl)morpholine

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Reaction Steps

Dissolve 2-(3-methoxyphenyl)-4-(4-nitrophenyl)sulfonyl-morpholine (11.2 g, 29.6 mmol) in ACN (150 mL) and water (2.67 mL). Add LiOH (6.21 g, 147.99 mmol) while stirring the mixture and followed by 1-propanethiol (13.42 mL, 147.99 mmol). Stir the mixture for 25 h at ambient temperature. Dilute the mixture with EtOAc and add brine. Extract twice with EtOAc. Collect and concentrate the extracts to ˜200 mL under reduced pressure, then wash three times with 1N HCl. Combine the aqueous acid extracts and add Na2CO3 until the mixture is basic. Extract the basic solution three times with EtOAc; combine the extracts; wash the extracts with brine; and dry over Na2SO4. Filter; collect the filtrate; and remove the solvents under reduced pressure to provide a residue. Purify the residue via flash column chromatography eluting with EtOAc, followed by a 5-100% gradient of (10% 2M NH3 in MeOH)/DCM. Combine the product fractions, and remove the solvents under reduced pressure to provide the title compound as a yellow oil (3.09 g, 15.99 mmol). MS (m/z): 194 (M+1).

Provenance & Evidence