Water → HCID 72299201, compound

HRID 2177495Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][C:6]([N+:14]([O-:16])=[O:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][N:4]([CH3:17])[C:3]1=[O:18].[H-].[Na+].I[CH3:22].O>CN(C=O)C>[CH3:22][O:1][CH:2]1[CH2:7][C:6]([N+:14]([O-:16])=[O:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][N:4]([CH3:17])[C:3]1=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.15 g (4.595 mmol) rac-3-Hydroxy-1-methyl-5-nitro-5-phenyl-piperidin-2-one (example A.10, step 1) in 11.5 ml DMF was cooled to 0° C. 220 mg (5.514 mmol) NaH (60% in oil) was added. The temperature rose to 3° C. The mixture was stirred at 0° C. for 15 minutes. 430 ul (6.893 mmol) iodomethane was added and the mixture was stirred at 0° C. for 30 minutes. 6.5 ml water was added and the solvent was removed in vacuo. The residue was taken in ethyl acetate. The solution was washed twice with water. The washings were reextracted once with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 500 mg (42%) of the title compound as a light brown solid. MS (m/e): 265.1 (M+H).

Workup

customwas cooled to 0° C
customrose to 3° C
stirringthe mixture was stirred at 0° C. for 30 minutes
customthe solvent was removed in vacuo
washThe solution was washed twice with water
dry with materialThe combined extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record: ord-dd58900681834e69a45d718246dc4153
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067911B2

Reaction notes

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