Methanesulfonyl chloride → Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

HRID 2239561Notes

Reaction equation

HRID 2239561 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[CH3:14][S:15]([O:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylateYield 63.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 3-hydroxypyrrolidine-1-carboxylate (3.00 g, 16.02 mmol) was dissolved in dry DCM (50 mL) and cooled in an ice-water bath. Methanesulfonyl chloride (2.38 g, 20.83 mmol) was added followed by TEA (2.43 g, 24.03 mmol) and the reaction mixture was stirred at 0° C. for 3.5 h. The reaction mixture was washed with water (250 mL) and dried with MgSO4, filtered and evaporated. The crude product was purified using Biotage Horizon HPFC system (40+M column, isocratic run heptane/EtOAc (50:50)) affording the title compound (2.70 g, 63.5%). 1H NMR (500 MHz, CDCl3): δ 1.38 (s, 9H), 2.07 (bs, 1H), 2.18 (bs, 1H), 2.97 (s, 3H), 3.35-3.61 (m, 4H), 5.16-5.18 (m, 1H); 13C NMR (125 MHz, CDCl3): δ 28.59, 31.84, 32.76, 38.80, 43.61, 52.16, 80.12, 154.30.

Workup

  1. temperaturecooled in an ice-water bath
  2. washThe reaction mixture was washed with water (250 mL)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-d865b2cf74da45398eb848e13adcf3e0
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

Loading…