Sodium Hydroxide → HCID 131719404, compound

HRID 440516Notes

Reaction equation

HRID 440516 reaction equation
[BH4-].[Na+].[I-].[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1([C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[CH2:19][CH2:18][N+:17]=2[CH3:30])[CH2:15][CH2:14][CH2:13]1)#[N:5].[OH-].[Na+].[C:33]([C:41]([C:56]([OH:58])=[O:57])([OH:55])[C:42]([C:47](=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([OH:46])[C:43]([OH:45])=[O:44])(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(OCC)(=O)C.CCOCC.CC(O)C.CO>[C:47]([C:42]([C:43]([OH:45])=[O:44])([OH:46])[C:41]([C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([OH:55])[C:56]([OH:58])=[O:57])(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1([CH:16]2[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[CH2:19][CH2:18][N:17]2[CH3:30])[CH2:15][CH2:14][CH2:13]1)#[N:5]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 12362975HCID 12362975, compoundHCID 22406834HCID 22406834, compound

Product 1

HCID 131719404HCID 131719404, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (0.465 G) was added portionwise to a mixture of 1-[1-(2-cyanophenyl)cyclobutyl]-6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolinium iodide (6 g) and methanol (40 ml). The mixture was stirred for 2 hours then poured onto aqueous sodium hydroxide solution and the product extracted into ether. The solvent was removed from the extracts to give a gum which was dissolved in ethyl acetate and a little propan-2-ol. A 0.4M solution of (±)-dibenzoyltartaric acid in ether (35 ml) was added and the resulting suspension was concentrated in vacuo. The residual solid was washed with ether to give 1-[1-(2-cyanophenyl)cyclobutyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (±)-dibenzoyltartrate (7.2 g), m.p. 109°-112° C. (dec).

Workup

  1. extractionthe product extracted into ether
  2. customThe solvent was removed from the extracts
  3. customto give a gum which
  4. concentrationthe resulting suspension was concentrated in vacuo
  5. washThe residual solid was washed with ether

Sources & evidence

ORD record
ord-22404b8ce49e4e19b29caa03fde22e90
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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