HCID 748083, compound → (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

HRID 1732137Notes

Reaction equation

HRID 1732137 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]1

Participants

4

Reactant 2

HCID 748083HCID 748083, compoundHCID 4311764Sodium borohydride

Product 1

HCID 13375506(3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carbolineYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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%

Workup

  1. temperaturerefluxed for 1.5 hours
  2. filtrationThe insoluble materials are filtered off
  3. washwashed with hot ethanol
  4. distillationdistilled
  5. customto remove the solvent
  6. additionWater (40 ml) is added to the residue
  7. stirringthe solution is stirred for 40 minutes
  8. filtrationThe precipitates are collected by filtration
  9. customdried
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5edd9d6a424244c994f90faa1f2ceb54
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

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