Hydrochloric Acid → Ethyl 5-(cyclohexylmethyl)-1-(methylsulfonyl)piperidine-3-carboxylate

HRID 253104Notes

Reaction equation

C(N(CC)CC)C.[CH:8]1([CH2:14][CH:15]2[CH2:20][NH:19][CH2:18][CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].Cl>C(Cl)Cl>[CH:8]1([CH2:14][CH:15]2[CH2:20][N:19]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:18][CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (340 mL, 2.4 mmol) was added to a solution of ethyl 5-(cyclohexylmethyl)piperidine-3-carboxylate (155 mg, 0.60 mmol) and methanesulfonyl chloride (75 mL, 0.90 mmol) in CH2Cl2 (6 mL) cooled to 0° C. The reaction was maintained at this temperature for 15 min at which point the whole was allowed to warm to RT and stir for an additional 3 h. The reaction was diluted with CH2Cl2 (20 mL) and poured into HCl (1 N, 20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were sequentially washed with H2O (10 mL) and brine before being dried over Na2SO4. Concentration under reduced pressure provided the title compound. MS m/z: 332.1 (M+1).

Workup

temperatureThe reaction was maintained at this temperature for 15 min at which point the whole
temperatureto warm to RT
customThe layers were separated
extractionthe aqueous layer was extracted with CH2Cl2 (3×20 mL)
washThe combined organic layers were sequentially washed with H2O (10 mL) and brine
dry with materialbefore being dried over Na2SO4
concentrationConcentration under reduced pressure

Sources & evidence

ORD record: ord-7c2aed39b60548619ac1c74a43753772
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872009B2

Reaction notes

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