Methanesulfonyl chloride → Methanesulfonic acid 1-[1-(4-Chloro-phenyl)-cyclopentanecarbonyl]-piperidin-3-ylmethyl ester

HRID 1788081Notes

Reaction equation

HRID 1788081 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]([N:15]3[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][OH:22])[CH2:16]3)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:13]([N:15]3[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][O:22][S:33]([CH3:32])(=[O:35])=[O:34])[CH2:16]3)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 22335026[1-(4-Chloro-phenyl)-cyclopentyl]-(3-hydroxymethyl-piperidin-1-yl)-methanone

Product 1

HCID 21303199Methanesulfonic acid 1-[1-(4-Chloro-phenyl)-cyclopentanecarbonyl]-piperidin-3-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-(4-chloro-phenyl)-cyclopentyl]-(3-hydroxymethyl-piperidin-1-yl)-methanone (0.5 g, 1.55 mmol) in dichloromethane (9.5 mL) at room temperature was added iPr2NEt (0.5 g, 3.9 mmol) followed by MsCl (0.214 g, 1.86 mmol). The reaction mixture was allowed to stir for one hour before concentrating and purifying the resulting residue by silica gel chromatography (gradient 2.5-100% EtOAc in hexane). The desired compound was obtained as an oil (0.345 g, 56%). 13C (100 MHz, CDCl3, partial) δ 174.0, 144.0, 131.8, 128.8, 126.5, 70.8, 58.1, 35.3, 26.5, 24.9. 1H (300 MHz, CDCl3) δ 7.26-7.24 (m, 2H), 7.13-7.10 (m, 2H), 4.61-1.86 (m, 19H), 1.67 (s, 3H).

Workup

  1. concentrationbefore concentrating
  2. custompurifying the resulting residue by silica gel chromatography (gradient 2.5-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-c5434389f3a442329f8bdc103ff7daa9
Source dataset
uspto-grants-2009_03
Patent number
US07511141B2

Reaction notes

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