HCID 748083, compound → (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline
Reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@@H:3]([C:14](OC)=[O:15])[NH:2]1.[BH4-].[Na+]>C(O)C>[OH:15][CH2:14][C@@H:3]1[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1][NH:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 15 g of methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate, 6.99 g of NaBH4, and 225 ml of 80% ethanol is stirred at room temperaure for 12 hours, and then refluxed for 1.5 hours. The insoluble materials are filtered off and washed with hot ethanol. The filtrate and the washing are combined and distilled to remove the solvent. Water (40 ml) is added to the residue, and the solution is stirred for 40 minutes. The precipitates are collected by filtration, dried and then recrystallized from ethanol. 9.03 g of (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline are obtained as colorless needles. Yield: 79.4%