Sulfuric Acid → (RS)-3-hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline

HRID 262112Notes

Reaction equation

HRID 262112 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].O[CH2:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][NH:9]1>O>[OH:4][S:1]([O:3][CH2:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][NH:9]1)(=[O:2])=[O:5]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 3752277(1,2,3,4-Tetrahydro-isoquinolin-3-yl)-methanol

Product 1

HCID 21320142(RS)-3-hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

34 N Sulphuric acid (d=1.83; 36.8 cc) is added, over a period of a few minutes, to a suspension of (RS)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (106 g) in water (226 cc). The temperature rises to 60° C. and the solid goes into solution. The mixture is heated at 100°-110° C. whilst water is distilled off, and then at 160° C. whilst concentrating under reduced pressure (20 mm Hg). The concentration process is concluded under a pressure of 1mm Hg. The residue crystallises on cooling. Crude (RS)-3-hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline (151 g) is thus obtained in the form of pale yellow crystals.

Workup

  1. customrises to 60° C.
  2. distillationis distilled off
  3. concentrationat 160° C. whilst concentrating under reduced pressure (20 mm Hg)
  4. customThe residue crystallises
  5. temperatureon cooling

Sources & evidence

ORD record
ord-b42921c1227a4739beabcef2cd9152c2
Source dataset
uspto-grants-1979_05
Patent number
US04153698

Reaction notes

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