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

HRID 1029631Notes

Reaction equation

HRID 1029631 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

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-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-1-t-butoxycarbonyl-3-hydroxypyrrolidine (32 g) in dichloromethane (300 ml) were added triethylamine (28.6 ml) and then methanesulfonyl chloride (14.6 ml) under nitrogen at -10° C. After stirring at 0° C. for 30 minutes, the solution was washed in turn with water, 1N-hydrochloric acid solution, saturated sodium bicarbonate, and brine. The dried solution was evaporated to give (R)-1-t-butoxycarbonyl-3-methanesulfonyloxypyrrolidine (45 g).

Workup

  1. customat -10° C
  2. washthe solution was washed in turn with water, 1N-hydrochloric acid solution, saturated sodium bicarbonate, and brine
  3. customThe dried solution was evaporated

Sources & evidence

ORD record
ord-f079436c98d0434ba024715bbdd24092
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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