Hydrogen Bromide → HCID 22406856, compound

HRID 440495Notes

Reaction equation

HRID 440495 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][NH:15][CH:16]2[C:19]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29][CH3:30])[CH2:22][CH2:21][CH2:20]2)=[CH:11][C:10]=1[O:31][CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:35]([BH3-])#N.[Na+].Br>CC(O)C.CO>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][N:15]([CH3:35])[CH:16]2[C:19]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29][CH3:30])[CH2:20][CH2:21][CH2:22]2)=[CH:11][C:10]=1[O:31][CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22406890HCID 22406890, compound

Product 1

HCID 22406856HCID 22406856, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 7-benzyloxy-6-methoxy-1-[1-(2-methylthiophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline. (1.89 g), 37% aqueous formaldehyde solution (3 ml), methanol (30 ml) and sodium cyanoborohydride (0.5 g) was stirred at ambient temperature for 24 hours. The mixture was poured onto water (100 ml) and extracted with dichloromethane (300 ml). The extract was washed with dilute aqueous ammonia solution to yield a residue which was dissolved in propan-2-ol and treated with 48% aqueous hydrobromic acid. The solvent was removed by evaporation to yield 7-benzyloxy-6-methoxy-2-methyl-1-[1-(2-methylthiophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline which was used without further purification.

Workup

  1. additionThe mixture was poured onto water (100 ml)
  2. extractionextracted with dichloromethane (300 ml)
  3. washThe extract was washed with dilute aqueous ammonia solution
  4. customto yield a residue which
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-d986175af8e0431cbdc88b86b54dd354
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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