Acetic Acid → HCID 22406890, compound

HRID 440494Notes

Reaction equation

HRID 440494 reaction equation
C([BH3-])#N.[Na+].[CH2:5]([O:12][C:13]1[CH:22]=[C:21]2[C:16]([CH2:17][CH2:18][N:19]=[C:20]2[C:23]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[S:33][CH3:34])[CH2:26][CH2:25][CH2:24]2)=[CH:15][C:14]=1[O:35][CH3:36])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)(=O)C.Br>CC(O)C.CO>[CH2:5]([O:12][C:13]1[CH:22]=[C:21]2[C:16]([CH2:17][CH2:18][NH:19][CH:20]2[C:23]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[S:33][CH3:34])[CH2:24][CH2:25][CH2:26]2)=[CH:15][C:14]=1[O:35][CH3:36])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 5003444Sodium cyanoborohydrideHCID 224068867-Benzyloxy-6-methoxy-1-[1-(2-methylthiophenyl)cyclobutyl]-3,4-dihydroisoquinoline

Product 1

HCID 22406890HCID 22406890, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

Sodium cyanoborohydride (0.8 g) was added to a mixture of 7-benzyloxy-6-methoxy-1-[1-(2-methylthiophenyl)cyclobutyl]-3,4-dihydroisoquinoline (2.8 g, prepared as described in Example CA32), acetic acid (20 ml) and methanol (10 ml) at 0° C. and stirred for 60 hours at ambient temperature. The mixture was poured onto water (300 ml) and extracted with dichloromethane. The organic layer was washed with aqueous ammonia solution (100 ml), then brine (100 ml), and dried over magnesium sulphate. The solvent was removed by evaporation to yield a gum. The gum was dissolved in propan-2-ol and treated with excess 48% aqueous hydrobromic acid. Evaporation of the solvent yielded a solid which was triturated with petroleum ether (b.p. 60°-80° C.), then isolated by filtration to give 7-benzyloxy-6-methoxy-1-[1-(2-methylthiophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. additionThe mixture was poured onto water (300 ml)
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with aqueous ammonia solution (100 ml)
  4. dry with materialbrine (100 ml), and dried over magnesium sulphate
  5. customThe solvent was removed by evaporation
  6. customto yield a gum
  7. customEvaporation of the solvent
  8. customyielded a solid which
  9. customwas triturated with petroleum ether (b.p. 60°-80° C.)
  10. customisolated by filtration

Sources & evidence

ORD record
ord-d6350718e49a4f2b8766c8c3e186fc79
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

Loading…