Hydrochloric Acid → (S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1280738Notes

Reaction equation

HRID 1280738 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(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.Cl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:36]([C:33]2[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=2)(=[O:38])=[O:37])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 57957824(S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (8.5 g, 45.4 mmol), triethylamine (9.47 ml, 68.1 mmol) and dimethylaminopyridine (0.55 g, 4.5 mmol) in CH2Cl2 (150 ml) was added portionwise p-toluenesulfonyl chloride (9.52 g, 49.9 mmol). After 48 hours stirring at room temperature, reaction mixture was acidified to pH 1 with 1N HCl and aqueous phase was extracted with CH2Cl2. Combined organic phases were washed with 1N HCl and H2O, dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1 then 8:2 then 1:1) to provide (S)-3-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (13.1 g, 87%) as a slightly yellow oil, MS: m/e=268.1 (M-OtBu) and [α]D20=+17.55° (c=3.33, diethylether).

Workup

  1. customreaction mixture
  2. extractionwas extracted with CH2Cl2
  3. washCombined organic phases were washed with 1N HCl and H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed over silica gel (hexane-ethylacetate 9:1

Sources & evidence

ORD record
ord-25a4b3cb5fc4483b802789e5201e16dd
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

Loading…