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0 °C

Add trifluoroacetic acid (5.5 ml, 71 mmol) to a stirred solution of [3-(benzo[b]thiophen-4-yloxy)-4-cyclohexyl-butyl]-methyl-carbamic acid tert-butyl ester (1.49 g, 3.6 mmol) and dichloromethane (80 ml) at 0° C. under N2. Stir for 5 minutes at 0° C. and allow the reaction to reach room temperature. Stir for 90 minutes, add sodium bicarbonate. Partition between sodium bicarbonate and dichloromethane, wash the combined dichloromethane layers with brine, dry over sodium sulfate. Filter and concentrate to give the crude compound. Purify the compound by flash chromatography, eluting with 3% ethanol/0.3% ammonium hydroxide/chloroform to yield 0.511 g (45%) of the title compound: mass spectrum (ion spray) m/z=318 (M+1); HPLC (90/5/5 to 0/95/5 water/acetonitrile/5% formic acid) Xterra MS C18 2.1 mm×50 mm×3.5micron: Retention time 3.08 minutes, Purity 100%.

1. customthe reaction
2. customto reach room temperature
3. stirringStir for 90 minutes
4. customPartition between sodium bicarbonate and dichloromethane
5. washwash the combined dichloromethane layers with brine
6. dry with materialdry over sodium sulfate
7. filtrationFilter
8. concentrationconcentrate
9. customto give the crude compound
10. customPurify the compound by flash chromatography
11. washeluting with 3% ethanol/0.3% ammonium hydroxide/chloroform