(2,5-Dimethylphenyl)acetyl chloride → HCID 66794133, compound

HRID 2035299Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([OH:14])[CH2:11][CH2:10][N:9]([O:12][CH3:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].CN(C)C1C=CN=CC=1.CN(C1C=CN=CC=1)C.[CH3:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][C:35]=1[CH2:41][C:42](Cl)=[O:43]>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([O:14][C:42](=[O:43])[CH2:41][C:35]2[CH:36]=[C:37]([CH3:40])[CH:38]=[CH:39][C:34]=2[CH3:33])[CH2:7][CH2:8][N:9]([O:12][CH3:13])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-hydroxy-1-methoxy-piperidine-4-carboxylic acid ethyl ester (1.0 g, 4.92 mmol) in 10 ml pyridine under argon was added 4-dimethylaminopyridine DMAP (30 mg, 0.25 mmol). The solution was cooled down to 0° C., then (2,5-dimethyl-phenyl)-acetyl chloride (0.99 g, 5.4 mmol) was added dropwise. The reaction mixture was warmed up to room temperature and left stirring for 5 days. Then the reaction mixture was concentrated and the crude product was purified by column chromatography on silica gel (ethyl acetate/cyclohexane first 1:15, then 1:9) to give pure 4-[2-(2,5-dimethyl-phenyl)-acetoxy]-1-methoxy-piperidine-4-carboxylic acid ethyl ester (compound P3.2) as light yellow oil. Yield: 530 mg.

Workup

temperatureThe reaction mixture was warmed up to room temperature
waitleft
concentrationThen the reaction mixture was concentrated
customthe crude product was purified by column chromatography on silica gel (ethyl acetate/cyclohexane first 1:15

Sources & evidence

ORD record: ord-12db9e4a17a34c36982881ee8abcb862
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08574607B2

Reaction notes

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