Hydrochloric Acid → HCID 51357960, compound

To a stirred solution of [(2S,5R)-5-methyl-4-(phenylmethyl)-2-morpholinyl]methanol (1.05 g, 4.74 mmol) in ethanol (15 mL) was added hydrochloric acid (concentrated, 12M) (0.435 mL, 5.22 mmol). The mixture was purged with nitrogen to degas, then 10% palladium on carbon (Degussa Type E101 NE/W, 50% wet) (150 mg, 0.070 mmol) was added and the mixture was purged with hydrogen and then stirred under the balloon. After stirring 4 hrs, TLC (50% EtOAc-hexanes) showed no starting material, and baseline product. The mixture was degassed with nitrogen, filtered through Celite, and evaporated to dryness to afford the title compound (880 mg) as the hydrochloride salt. 1H NMR (400 MHz, D2O): δ 3.72-3.92 (m, 3H), 3.48-3.69 (m, 3H), 3.13-3.24 (m, 1H), 3.04-3.13 (m, 1H), 1.34 (d, J=7.1 Hz, 3H).

1. customThe mixture was purged with nitrogen
2. customto degas
3. customthe mixture was purged with hydrogen
4. stirringAfter stirring 4 hrs
5. customThe mixture was degassed with nitrogen
6. filtrationfiltered through Celite
7. customevaporated to dryness

ORD record

ord-e5272ed190d54f5cbe621f44c0b12d8c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697685B2