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

HRID 893386Notes

Reaction equation

HRID 893386 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(OCC)(=O)C.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 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 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A dry 10 gallon glass-lined vessel was charged with the alcohol (2) (3.39 kg d.b., 18.1 Mol) and ethyl acetate (50 l) under nitrogen. The solution was cooled to -5° C. and triethylamine (Lancaster B/N 076337, 5.1 l) was added in one portion. Methanesulphonyl chloride (Lancaster B/N 79561, 1.68 l, 21.7 Mol) was added dropwise over 1 h, maintaining the reaction temperature at -5°-2° C. On complete addition, the slurry was aged at -5° C. for 30 min. Water (20 1) was added over 10 min and the phases well mixed The aqueous layer was separated and the organics washed with 1M aqueous hydrochloric acid (10 l), saturated sodium bicarbonate (10 1) and dried (Na2SO4). Solvent evaporation gave the product as a pale yellow oil.

Workup

  1. temperaturemaintaining the reaction temperature at -5°-2° C
  2. additionOn complete addition
  3. additionthe phases well mixed The aqueous layer
  4. customwas separated
  5. washthe organics washed with 1M aqueous hydrochloric acid (10 l), saturated sodium bicarbonate (10 1)
  6. dry with materialdried (Na2SO4)
  7. customSolvent evaporation

Sources & evidence

ORD record
ord-a8d01fc645b04d56b969e56d60cd102d
Source dataset
uspto-grants-1992_06
Patent number
US05124460

Reaction notes

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