Methanesulfonyl chloride → HCID 66875213, compound

HRID 889057Notes

Reaction equation

HRID 889057 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10]O)[CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4].[CH3:19][S:20](Cl)(=[O:22])=[O:21].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][S:20]([CH3:19])(=[O:22])=[O:21])[CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 235957531-(tert-Butyl) 2-methyl 4-(hydroxymethyl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 66875213HCID 66875213, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.5 g, 1.93 mmol) and TEA (0.33 gm, 2.89 mmol) in DCM (20 ml), methane sulphonyl chloride (0.38 g, 3.86 mmol) was added at 0° C. The reaction mixture was stirred at room temperature for 4 h. Aqueous NaHCO3 solution was added to it and extracted with DCM. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to offer 4-methanesulfonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester as a yellow solid (0.45 g, 69%). 1HNMR (400 MHz, CDCl3): δ 1.45-1.50 (Two s, 9H); 1.79-1.85 (m, 1H); 2.42-2.81 (m, 2H); 3.08 (s, 3H); 3.21-3.38 (m, 1H); 3.77 (s, 3H); 4.09-4.4 (m, 3H).

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a1a35429a82743929829aa8741f66271
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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