Triethylamine → 3-(Methoxycarbonyl)cyclopentyl methanesulfonate

HRID 1367471Notes

Reaction equation

HRID 1367471 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6]1)=[O:4].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([O:10][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 520596Cyclopentanecarboxylic acid, 3-hydroxy-, methyl ester

Product 1

HCID 205054773-(Methoxycarbonyl)cyclopentyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 3-hydroxy-cyclopentanecarboxylic acid methyl ester (1.6 g, 1.0 eq, cis/trans-mixture from step 1) in dichloromethane (25 mL) was cooled to −20° C. and treated with triethylamine (1.4 g, 1.3 eq) and methansulfonyl chloride (1.5 g, 1.2 eq). The mixture was stirred at −20° C. for 20 min and then partitioned between water and dichloromethane. The organic phase was washed with brine, dried over sodium sulfate and evaporated. The title compound was obtained as a yellow liquid (2.4 g, 97%) and was used crude in the next step.

Workup

  1. custompartitioned between water and dichloromethane
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-0920ecc280f044808bd66ae53ea1ce37
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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