Water → tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

HRID 45582

Reaction equation

HRID 45582 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N(CC)CC)C.O>ClCCl.CN(C)C1C=CN=CC=1>[S:21]([O:11][CH2:10][C@@H:9]1[CH2:12][CH2:13][CH2:14][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 11783214tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of N-Boc-L-prolinol (51.2 g, 254 mmol) in dichloromethane (250 mL) was cooled to 0° C., and thereto were added p-toluenesulfonylchloride (53.4 g, 280 mmol), triethylamine (30.9 g, 42.6 mL, 305 mmol), and 4-dimethylaminopyridine (5.00 g, 40.9 mmol). After stirring overnight at room temperature, to the mixture was added water, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified with silica gel column (hexane/ethyl acetate=70/30 to 30/70) to give the title compound (89.7 g, 250 mmol, 99%).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified with silica gel column (hexane/ethyl acetate=70/30 to 30/70)

Sources & evidence

ORD record
ord-b59673d570cf48c78b6d783fc4727013
Source dataset
uspto-grants-2013_09
Patent number
US08541585B2

Linked notes

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