Water → Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

HRID 2403230Notes

Reaction equation

HRID 2403230 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.C(N(CC)CC)C.[S:21](Cl)([CH3:24])(=[O:23])=[O:22].O>C(Cl)Cl>[CH3:24][S:21]([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:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylateYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (Aldrich; 7.42 g, 39.6 mmol), in DCM (20 mL) was added, at 0° C., triethylamine (8.44 mL; 48.5 mmol) and then mesylchloride (3.13 mL; 40 mmol). The mixture was stirred for 18 hours at RT and then water was added and the product was extracted with DCM (3×20 mL). The combined organic fractions were dried (MgSO4), filtered and the solvent removed in vacuo to give tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate (8.26 g; 77%) as a brown oil. 1H NMR: (CDCl3, 400 MHz) δ 5.27-5.20 (1 H, m), 3.70-3.49 (4 H, m), 3.04 (3 H, s), 2.90-2.05 (2 H, m), 1.46 (9 H, s).

Workup

  1. extractionthe product was extracted with DCM (3×20 mL)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b256a0b72f5e4de88e7294b2a7eb7f77
Source dataset
uspto-grants-2014_08
Patent number
US08802663B2

Reaction notes

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