4-Toluenesulfonyl chloride → tert-Butyl 3-(tosyloxy)pyrrolidine-1-carboxylate

HRID 2194558Notes

Reaction equation

HRID 2194558 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.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[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)([C:18]1[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 13591085tert-Butyl 3-(tosyloxy)pyrrolidine-1-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (0.9 g, 5.02 mmol) in anhydrous pyridine (10 mL) at 0° C. was added 4-methylbenzene-1-sulfonyl chloride (1.0 g, 5.27 mmol). The suspension was allowed to warm to room temperature and stirred for 24 h. After this time, the suspension was poured onto crushed ice and extracted with EtOAc. The organic layer was separated, washed with water, brine, dried (MgSO4) and concentrated under reduced pressure to give the title compound (15) (1.1 g, 69%) as a light yellow colored solid. 1H NMR (CDCl3, 400 MHz) δ 7.79 (d, J=8.3 Hz, 2H), 7.35 (d, J=8.0 Hz, 2H), 4.94-5.17 (m, 1H), 3.33-3.56 (m, 4H), 2.46 (s, 3H), 1.79-2.28 (m, 2H), 1.43 (s, 9H); MS (APCI, M+H+) C16H24NO5S, calcd. 342.1. found 286.1.

Workup

  1. additionAfter this time, the suspension was poured
  2. customonto crushed ice
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4cf1afcdbcc34b24b2a8b9d8d97d48f7
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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