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

HRID 262110노트

반응식

HRID 262110 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
110 °C

실험 절차

A solution of (S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (41 g) in a mixture of 34 N sulphuric acid (13 cc) and water (70 cc) is heated at 110° C. Water (about 50 cc) is distilled off and the residue is then concentrated at 100° C. under reduced pressure (20 mm Hg). The brown oily residue is taken up in a mixture of 34 N sulphuric acid (13 cc) and water (70 cc). Water (50 cc) is again distilled off, the mixture is then concentrated as described above, and the concentration process is concluded 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 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.

후처리

  1. distillationWater (about 50 cc) is distilled off
  2. concentrationthe residue is then concentrated at 100° C. under reduced pressure (20 mm Hg)
  3. additionThe brown oily residue is taken up in a mixture of 34 N sulphuric acid (13 cc) and water (70 cc)
  4. distillationWater (50 cc) is again distilled off
  5. concentrationthe mixture is then concentrated
  6. customis concluded at 100° C. under reduced pressure (1 mm Hg)
  7. customThe residue, which crystallises
  8. temperatureon cooling
  9. customis recrystallised from a mixture of ethanol (140 cc) and water (60 cc)
  10. temperatureAfter cooling for 15 hours at about 5° C.
  11. filtrationthe resulting crystals are filtered off
  12. washwashed with a mixture (20 cc) of ethanol and water (3-1 by volume)
  13. customAfter drying at 60° C. under reduced pressure (1 mm Hg)

출처 및 근거

ORD 기록
ord-d7e6f4b5627544f98b85172f99c8d8b9
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04153698

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