Sulfuric Acid → (S)-3-hydroxysulphonyloxymethyl1,2,3,4-tetrahydroisoquinoline

HRID 461808Notes

Reaction equation

HRID 461808 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][NH:4]1.[S:13](=O)(=[O:16])([OH:15])[OH:14]>O>[OH:16][S:13]([O:1][CH2:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][NH:4]1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 776757[(3S)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol

Product 1

HCID 54239900(S)-3-hydroxysulphonyloxymethyl1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A solution of (S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (41 g.) in a mixture of sulphuric acid (d = 1.83; 13 cc.) and water (70 cc.) is heated at 110° C. Water (about 50 cc.) is distilled off and the mixture is then concentrated under reduced pressure (20 mm. Hg) at 100° C. The brown oily residue is taken up in a mixture of sulphuric acid (d = 1.83; 13 cc. ) and water (70 cc.); water (50 cc.) is again distilled off and the mixture is then concentrated as previously described, after which the concentration is finished at 100° C. under reduced pressure (1 mm. Hg). The residue, which crystallises on cooling, is recrystallised from a mixture of ethanol (140 cc.) and water (60 cc.) After cooling for 15 hours at about 5° C., the crystals which have appeared are filtered off and washed with a mixture of ethanol and water (3:1 by volume) (20 cc.) and then with ethanol (2 × 25 cc.). After drying at 60° C . under reduced pressure (1 mm. Hg), (S)-3-hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline (48 g.) is obtained in the form of white crystals.

Workup

  1. distillationWater (about 50 cc.) is distilled off
  2. concentrationthe mixture is then concentrated under reduced pressure (20 mm. Hg) at 100° C
  3. additionThe brown oily residue is taken up in a mixture of sulphuric acid (d = 1.83; 13 cc. ) and water (70 cc.)
  4. distillationwater (50 cc.) is again distilled off
  5. concentrationthe mixture is then concentrated
  6. concentrationafter which the concentration
  7. customis finished at 100° C. under reduced pressure (1 mm. Hg)
  8. customThe residue, which crystallises
  9. temperatureon cooling
  10. customis recrystallised from a mixture of ethanol (140 cc.) and water (60 cc.)
  11. temperatureAfter cooling for 15 hours at about 5° C.
  12. filtrationthe crystals which have appeared are filtered off
  13. washwashed with a mixture of ethanol and water (3:1 by volume) (20 cc.)
  14. customAfter drying at 60° C

Sources & evidence

ORD record
ord-774114fada9c4372b5a402cad65bd83f
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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