Ammonium Hydroxide → HCID 86754619, compound

HRID 1739778Notes

Reaction equation

HRID 1739778 reaction equation
[B].C[O:3][C:4]1[CH:5]=[C:6]([C@@:10]23[CH2:19][C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:17][CH2:16][C@H:15]2[CH2:14][N:13]([CH3:26])[CH2:12][CH2:11]3)[CH:7]=[CH:8][CH:9]=1.[NH4+].[OH-]>C(Cl)(Cl)Cl>[OH:3][C:4]1[CH:5]=[C:6]([C@@:10]23[CH2:19][C:18]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:17][CH2:16][C@H:15]2[CH2:14][N:13]([CH3:26])[CH2:12][CH2:11]3)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 5462311BoronHCID 86754618HCID 86754618, compound

Product 1

HCID 86754619HCID 86754619, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2.7 ml (29 mmol) of boron uibromide were dissolved in 85 ml of dry CHCl3 under a nitrogen atmosphere. 1.6 g (4.8 mmol) of (±)-trans4a-(3-methoxyphenyl)-2-methyl-6-phenyl-1,2,3,4,4a,5,8,8a-octahydroisoquinoline dissolved in 17 ml of dry CHCl3 were added dropwise at room temperature. After 2 h the reaction mixture was poured onto 85 g of crushed ice containing 8.5 ml of conc. NH4OH and stirred 20 min. The phases were separated, the organic phase was dried over Na2SO4 and the solvent removed in vacuo. The residue was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 82:13:0.8 respectively. The resulting solid was triturated with acetone, filtered, washed and dried, yielding 0.6 g of the title compound. M.p.=243-246° C.

Workup

  1. additionwere added dropwise at room temperature
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with a mixture CH2Cl2 /MeOH/conc
  7. customThe resulting solid was triturated with acetone
  8. filtrationfiltered
  9. washwashed
  10. customdried

Sources & evidence

ORD record
ord-adf67f88f85f47daa4c7d51932ebfa67
Source dataset
uspto-grants-1999_10
Patent number
US05968949

Reaction notes

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