Acetic Acid → HCID 22406840, compound

HRID 440484Notes

Reaction equation

HRID 440484 reaction equation
C([BH3-])#N.[Na+].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1([C:15]2[C:24]3[C:19](=[CH:20][C:21]([F:27])=[C:22]([O:25][CH3:26])[CH:23]=3)[CH2:18][CH2:17][N:16]=2)[CH2:14][CH2:13]1.C(O)(=O)C.[OH-].[Na+]>CO>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1([CH:15]2[C:24]3[C:19](=[CH:20][C:21]([F:27])=[C:22]([O:25][CH3:26])[CH:23]=3)[CH2:18][CH2:17][NH:16]2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22406749HCID 22406749, compound

Product 1

HCID 22406840HCID 22406840, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (10.7 g) was added at 0° C. to a mixture of 1-[1-(2-chlorophenyl)cyclopropyl]-6-fluoro-7-methoxy-3,4-dihydroisoquinoline (26.7 g, prepared in a similar manner to that described above), acetic acid (185 ml) and methanol (95 ml) under nitrogen. The mixture was allowed to reach ambient temperature and was stirred for 22 hours. The mixture was poured onto water, and solid sodium hydroxide (150 g) in ice-water (500 ml) was added. The product was extracted into ether and the solvent then removed in vacuo to yield 1-[1-(2-chlorophenyl)cyclopropyl]-6-fluoro-7-methoxy-1,2,3,4-tetrahydroisoquinoline as a gum.

Workup

  1. customprepared in a similar manner to that
  2. customto reach ambient temperature
  3. additionwas added
  4. extractionThe product was extracted into ether
  5. customthe solvent then removed in vacuo

Sources & evidence

ORD record
ord-53fbd4674cd04001afb9e599df1592d2
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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