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

HRID 2420098Notes

Reaction equation

HRID 2420098 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 (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 redissolved in a hot mixture of ethanol (140 cc) and water (60 cc). After cooling for 15 hours at about 5° C the resulting crystals are filtered off and washed with a mixture (20 cc) of ethanol and water (3:1 by volume) 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 (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. dissolutionis redissolved in a hot mixture of ethanol (140 cc) and water (60 cc)
  11. temperatureAfter cooling for 15 hours at about 5° C the resulting crystals
  12. filtrationare filtered off
  13. washwashed with a mixture (20 cc) of ethanol and water (3:1 by volume)
  14. customAfter drying at 60° C under reduced pressure (1 mm Hg)

Sources & evidence

ORD record
ord-7672f9da521e41eb91300773f9f1f6d8
Source dataset
uspto-grants-1978_08
Patent number
US04108999

Reaction notes

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