Sodium Carbonate → (RS)-3-(4-hydroxy-phenylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1280736Notes

Reaction equation

HRID 1280736 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[SH:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([S:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2401474-MercaptophenolHCID 13591085tert-Butyl 3-(tosyloxy)pyrrolidine-1-carboxylate

Product 1

HCID 69926448(RS)-3-(4-hydroxy-phenylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(RS)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.8 g, 2.34 mmol), 4-mercaptophenol (0.49 g, 3.88 mmol, 90%) and Na2CO3 (0.37 g, 3.51 mmol) were suspended in acetonitrile (10 ml). After 20 hours refluxing, reaction mixture was concentrated. The residue was taken up in H2O (15 ml) and extracted with CH2Cl2 (3 times). The combined organic phases were dried over Na2SO4, filtered and the solvent was evaporated. The residue was chromatographed over silica gel (hexane-ethylacetate 4:1 then 2:1) to provide (RS)-3-(4-hydroxy-phenylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.56 g, 81%) as a slightly yellow solid, MS: m/e=296.4 (M+H+).(RS)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester is a known compound and has been prepared as described in WO 9734895.

Workup

  1. temperatureAfter 20 hours refluxing
  2. customreaction mixture
  3. concentrationwas concentrated
  4. extractionextracted with CH2Cl2 (3 times)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was chromatographed over silica gel (hexane-ethylacetate 4:1

Sources & evidence

ORD record
ord-1b97a2274e1246f4bdd7882146be4546
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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