(3S)-2-((tert-butoxy)carbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid → (S)-2-t-Butoxycarbonyl-1,2,3,4-tetrahydro-3-hydroxymethyl-7-hydroxyisoquinoline

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Reaction Steps

(S)-2-t-Butoxycarbonyl-1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid (100 mmol) is dissolved in THF (1 L). Borane methyl sulfide complex (200 mmol) is added carefully, and the solution heated at reflux for 1 hour. The solution is cooled, quenched with MeOH, and 1 N HCl to pH 2. The solution is neutralized to pH 7-8 with NaHCO3 and the solvent evaporated. The oily residue is diluted with water, extracted with EtOAC, washed with NaHCO3 and brine, then dried with MgSO4 and evaporated to give the title compound.

Provenance & Evidence