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

HRID 79303Notes

Reaction equation

HRID 79303 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.[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:14][S:15]([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:17])=[O:16]

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 106.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (87 mg, 0.465 mmol) in DCM (2 mL) at 0° C. was added methanesulfonyl chloride (58.5 mg, 0.511 mmol) and triethylamine (56.4 mg, 0.558 mmol). The cold bath was removed and the reaction was stirred for 30 minutes. The reaction was diluted with 5 mL DCM, washed with water and brine, dried (Na2SO4) and concentrated to give final product (131 mg).

Workup

  1. customThe cold bath was removed
  2. additionThe reaction was diluted with 5 mL DCM
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a359064b91246489d54f87d757c0d18
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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