Triethylamine → Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

HRID 2409092Notes

Reaction equation

HRID 2409092 reaction equation
[OH:1][C@@H: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.CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([O:1][C@@H: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:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 10934372Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (5.0 g, 26.7 mmol) and Et3N (8.0 g, 80.2 mmol) were dissolved in dichloromethane (50 mL). The mixture was stirred at 0° C. for 30 minutes, then methanesulfonyl chloride (4.5 g, 40.1 mmol) was added dropwise. It was stirred at room temperature for 2 h and concentrated under reduced pressure. DCM (50 mL) and water (50 mL) were added. The organic phase was washed with saturated NaHCO3 (30 mL) and H2O (2×30 mL), and concentrated to afford the title compound as oil (6 g, 100%).

Workup

  1. stirringIt was stirred at room temperature for 2 h
  2. concentrationconcentrated under reduced pressure
  3. additionDCM (50 mL) and water (50 mL) were added
  4. washThe organic phase was washed with saturated NaHCO3 (30 mL) and H2O (2×30 mL)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db412ffc8112429294177e33b2c6f455
Source dataset
uspto-grants-2014_08
Patent number
US08815882B2

Reaction notes

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