Methanesulfonyl chloride → 3-Pyrrolidinol, 1-(phenylmethyl)-, 3-methanesulfonate, (3R)-

HRID 2375447Notes

Reaction equation

HRID 2375447 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CN=C(N)C=1C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(N(CC)CC)C.ClCCl>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinolHCID 110078842-Amino-3,4-dimethylpyridine

Product 1

HCID 118072543-Pyrrolidinol, 1-(phenylmethyl)-, 3-methanesulfonate, (3R)-Yield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

The compound (3R)-1-benzyl-pyrrolidin-3-ol (1.0 g, 5.65 mM) was dissolved in triethylamine (2.0 ml, 14.3 mM), and dimethyl amino pyridine (DMAP) (0.002 g), dichloromethane (20.0 ml) and methanesulfonyl chloride (0.9 ml, 11.7 mM) was added dropwise at 0-5° C. The reaction mixture was maintained at the same temperature for about half an hour. The reaction mixture was then stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane (50.0 ml), washed with saturated sodium bicarbonate and brine solution. It was further dried over anhydrous sodium sulphate and concentrated to get the title compound as oil. Yield=95% (1.2 g, 5.38 mM). This material was used as such in the next step.

Workup

  1. temperatureThe reaction mixture was maintained at the same temperature for about half an hour
  2. washwashed with saturated sodium bicarbonate and brine solution
  3. dry with materialIt was further dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c059a6b7591f4e3799a0dd23c0340a59
Source dataset
uspto-grants-2008_12
Patent number
US07465751B2

Reaction notes

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