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(3-Formyl-phenyl)-acetic acid methyl ester (0.64 g), acetic acid (0.18 mL) and 4-phenyl-piperidine (0.48 mL) were combined in dichloromethane (10 mL). After 1 hour, sodium triacetoxyborohydride (0.95 g) was added and the reaction stirred overnight. After 24 hours, the solvent was evaporated. The resultant residue was loaded onto a conditioned SCX cartridge (10 g, Varian) and washed with methanol (50 mL), then eluted with methanolic ammonia solution (2M, 50 mL). The elution fraction was evaporated and the residue was dissolved in ethanol (10 mL). Calcium chloride anhydrous (0.67 g) was added followed by sodium borohydride (0.45 g) and the resulting mixture stirred overnight. An aqueous potassium carbonate solution (2M, 50 mL) was added and the ethanol evaporated. The aqueous was extracted with ethyl acetate (3×50 mL) and the combined organics washed with water (50 mL), brine (50 mL), dried (sodium sulfate) and evaporated. The residue was redissolved in tetrahydrofuran (10 mL) and cooled to 0° C., under nitrogen. Borane-methyl sulfide complex (2M solution in tetrahydrofuran, 2.25 mL) was added and the resulting mixture stirred for 5 min. The tetrahydrofuran was evaporated and the residue purified on silica, eluting with diethyl ether: iso-hexane [1:1 to 1:0] to give subtitle product, as an oil 193 mg.

1. waitAfter 24 hours
2. customthe solvent was evaporated
3. washwashed with methanol (50 mL)
4. washeluted with methanolic ammonia solution (2M, 50 mL)
5. customThe elution fraction was evaporated
6. dissolutionthe residue was dissolved in ethanol (10 mL)
7. additionCalcium chloride anhydrous (0.67 g) was added
8. stirringthe resulting mixture stirred overnight
9. additionAn aqueous potassium carbonate solution (2M, 50 mL) was added
10. customthe ethanol evaporated
11. extractionThe aqueous was extracted with ethyl acetate (3×50 mL)
12. washthe combined organics washed with water (50 mL), brine (50 mL)
13. dry with materialdried (sodium sulfate)
14. customevaporated
15. dissolutionThe residue was redissolved in tetrahydrofuran (10 mL)
16. additionBorane-methyl sulfide complex (2M solution in tetrahydrofuran, 2.25 mL) was added
17. stirringthe resulting mixture stirred for 5 min
18. customThe tetrahydrofuran was evaporated
19. customthe residue purified on silica
20. washeluting with diethyl ether