Methanesulfonyl chloride → Tert-butyl 4-methylsulfonyloxy-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate

HRID 1792033Notes

Reaction equation

HRID 1792033 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH:9]1[CH2:18][OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH2:10][CH:9]1[CH2:18][O:19][S:21]([CH3:20])(=[O:23])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 214612722-(Hydroxymethyl)-4-(methanesulfonyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 73103977Tert-butyl 4-methylsulfonyloxy-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Hydroxymethyl)-4-(methanesulfonyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester (1.715 g) was dissolved in pyridine (20 ml), and methanesulfonylchloride (0.6 ml) was added thereto. The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate, and washed with 1 N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 2 g of the title compound.

Workup

  1. washwashed with 1 N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-098a1780650b479d922e2c00fd2fd91e
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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