Methanesulfonyl chloride → HCID 86717511, compound

HRID 712055Notes

Reaction equation

HRID 712055 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([O:10][CH3:11])=[O:9])[C@H:4]([O:12][CH3:13])[CH2:3]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>ClCCl>[CH3:13][O:12][C@@H:4]1[CH2:3][C@@H:2]([O:1][S:15]([CH3:14])(=[O:17])=[O:16])[CH2:7][CH2:6][C@H:5]1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86717512HCID 86717512, compound

Product 1

HCID 86717511HCID 86717511, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl (1R,2R,4S)-4-hydroxy-2-methoxycyclohexanecarboxylate (racemic) (1.50 g, 7.97 mmol) in dichloromethane (40 mL) was treated with methanesulfonyl chloride (1.23 mL, 15.9 mmol) dropwise at 0° C. The mixture was stirred at 0° C. for 2 h and partitioned between ethyl acetate and water. The organic phase was concentrated and purified on silica gel (eluting with 50% ethyl acetate in hexanes) to give the desired product (2.12 g, 91%). 1H NMR (400 MHz, CDCl3) δ 4.62 (1H, m), 3.71 (3H, s), 3.48 (1H, m), 3.33 (3H, s), 3.02 (3H, s), 2.64 (1H, m), 2.32 (1H, m), 2.19 (1H, m), 2.00 (1H, m), 1.60-1.42 (3H, m) ppm.

Workup

  1. custompartitioned between ethyl acetate and water
  2. concentrationThe organic phase was concentrated
  3. custompurified on silica gel (eluting with 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-697f9d2b2ede479b8aaf90a7c95fe418
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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