Triethylamine → 3-(Methoxycarbonyl)cyclopentyl methanesulfonate

HRID 355265Notes

Reaction equation

HRID 355265 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]1[CH2:11][CH2:10][CH:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:6][CH:7]1[CH2:11][CH2:10][CH:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

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

Product 1

HCID 205054773-(Methoxycarbonyl)cyclopentyl methanesulfonateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of methanesulfonyl chloride (4.7 ml, 60 mmol) in 25 ml of CH2Cl2 was added dropwise with stirring to a solution of methyl 3-hydroxycyclopentanecarboxylate (6.5 g, 45 mmol) and triethylamine (9.0 ml, 65 mmol) in CH2Cl2 (65 ml) at 0° C. The solution was stirred at 23° C. for 24 h and then washed with water (3×50 ml). The washes were extracted with CH2Cl2 and the combined organic extracts were dried, treated with charcoal and filtered. The solvent was evaporated in vacuo to give the title compound as a yellow liquid, 9.1 g (91% yield), and as a mixture of isomers: ir (liq.) νmax : 1730 cm-1 : 1Hmr (CDCl3) δ: 5.13 (m, 1H, H-3), 3.68 (2×s, 3H, CO2Me), 3.00 (s, 3H, SO3Me), 2.8 (m, 1H, H-1) and 2.4-1.7 ppm (m, 6H, CH2).

Workup

  1. washwashed with water (3×50 ml)
  2. extractionThe washes were extracted with CH2Cl2
  3. customthe combined organic extracts were dried
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-735e07dcd85d493f9f9584387540466d
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

Loading…