2-Thiophenecarboxaldehyde → 6-Hydroxy-2-(2-thienylmethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 2413492Notes

Reaction equation

HRID 2413492 reaction equation
C([BH3-])#N.[Na+].[OH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][NH:11][CH2:10][CH2:9]2.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=O.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C(O)C>[OH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][N:11]([CH2:21][C:17]1[S:16][CH:20]=[CH:19][CH:18]=1)[CH2:10][CH2:9]2

Participants

6

Reactant 4

HCID 73642-ThiophenecarboxaldehydeHCID 266981,2,3,4-Tetrahydroisoquinolin-6-olHCID 5003444Sodium cyanoborohydrideHCID 124969952-Methylbenzenesulfonic acid hydrate

Product 1

HCID 133618026-Hydroxy-2-(2-thienylmethyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.6 g of sodium cyanoborohydride is added to a solution of 1.5 g of 6-hydroxy-1,2,3,4-tetrahydroisoquinoline, 1.2 g of thiophene-2-aldehyde and 1.8 g of toluenesulfonic acid monohydrate in 30 ml of ethanol. The mixture is stirred at room temperature for 8 hours, the solvent is removed in vacuo, and the residue is taken up with water/methylene chloride. The organic phase is again skaken with water, dried and evaporated in a rotary evaporator. The crude oily product is purified by chromatography on silica gel using a mixture of ethyl acetate/methylene chloride in the ratio 1:2. 1.7 g of a colorless oil, which crystallizes on standing (69% of theory), is obtained. Melting point: 110°-112° C.

Workup

  1. customthe solvent is removed in vacuo
  2. customdried
  3. customevaporated in a rotary evaporator
  4. customThe crude oily product is purified by chromatography on silica gel using
  5. additiona mixture of ethyl acetate/methylene chloride in the ratio 1:2
  6. custom1.7 g of a colorless oil, which crystallizes
  7. customis obtained

Sources & evidence

ORD record
ord-65d91df25a2140999d49b3d6f954ff7c
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

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