Triethylamine → Methanesulfonic acid 1-naphthalen-1-yl-cyclopentylmethyl ester

HRID 2169376Notes

Reaction equation

[C:1]1([C:11]2([CH2:16][OH:17])[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[S:25](Cl)([CH3:28])(=[O:27])=[O:26].C(OCC)(=O)C>ClCCl.CCCCCC>[C:1]1([C:11]2([CH2:16][O:17][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (1-naphthalen-1-yl-cyclopentyl)-methanol (340) (9.0 g, 39.8 mmol) in dichloromethane (180 mL) was added triethylamine (11.0 mL, 79.5 mL) and the reaction mixture was cooled to 0° C. To this reaction mixture was added mesylchloride and stirring was continued at room temperature for 18 h (silica TLC, 10% ethyl acetate in hexane; Rf=0.2). The reaction mass was diluted with dichloromethane (100 mL), washed with water (2×100 mL) and brine (100 mL) and dried and concentrated in vacuum to get a crude mass which was purified by Combi-Flash using gradient eluent mixture of ethyl acetate and hexane to get pure methanesulfonic acid 1-naphthalen-1-yl-cyclopentylmethyl ester (341) (4.25 g, 35%) as a white solid.

Workup

washwashed with water (2×100 mL) and brine (100 mL)
customdried
concentrationconcentrated in vacuum
customto get a crude mass which
customwas purified by Combi-Flash
additiongradient eluent mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-f83c01625bf04d02949a4f2082ed7ef1
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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