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To a −60° C. solution of oxalylchloride (0.21 ml, 2.42 mmol) in dry CH2Cl2 (4 ml) was added a solution of DMSO (0.34 ml, 4.84 mmol) in CH2Cl2 (2 ml). After 5 minutes stirring, a solution of 2,2-difluoro-4-phenyl-butan-1-ol (0.41 g, 2.2 mmol) in CH2Cl2 was added dropwise at −60° C. After 15 minutes stirring, triethylamine (1.54 ml, 11 mmol) was added dropwise, the reaction mixture was allowed to warm up to room temperature and H2O (10 ml) was added. The aqueous phase was extracted with CH2Cl2 (3×20 ml).The combined organic phases were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was dissolved in 1,2-dichloroethane (15 ml) and added to a suspension of (3S)-4-(pyrrolidin-3-ylsulfanyl)-phenol hydrobromide (0.68 g, 2.2 mmol), triethylamine (0.31 ml, 2.2 mmol) and sodium triacetoxyborohydride (0.74 g, 3.30 mmol) in 1,2-dichloroethane (45 ml). Mixture was stirred at 65° C. for 2 hours and overnight at room temperature. H2O (30 ml) was added. The aqueous phase was extracted with CH2Cl2 (3×20 ml).The combined organic phases were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed over silica gel (hexane-ethylacetate 99:1 to 90:10) to provide (3S)-4-[1-(2,2-difluoro-4-phenyl-butyl)-pyrrolidin-3-ylsulfanyl]-phenol (0.55 g, 70%) as light yellow oil, MS: m/e=364.2(M+H+).

1. stirringAfter 15 minutes stirring
2. extractionThe aqueous phase was extracted with CH2Cl2 (3×20 ml).The combined organic phases
3. dry with materialwere dried over Na2SO4
4. filtrationfiltered
5. customthe solvent was removed in vacuo
6. dissolutionThe residue was dissolved in 1,2-dichloroethane (15 ml)
7. stirringMixture was stirred at 65° C. for 2 hours and overnight at room temperature
8. extractionThe aqueous phase was extracted with CH2Cl2 (3×20 ml).The combined organic phases
9. dry with materialwere dried over Na2SO4
10. filtrationfiltered
11. customthe solvent was removed in vacuo
12. customThe residue was chromatographed over silica gel (hexane-ethylacetate 99:1 to 90:10)