HCID 86754617, compound → HCID 86754618, compound

HRID 1739777Notes

Reaction equation

HRID 1739777 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(O)[CH2:16][CH2:15][C@H:14]2[CH2:13][N:12]([CH3:26])[CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1>Cl>[NH4+:12].[OH-:2].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][CH2:15][C@H:14]2[CH2:13][N:12]([CH3:26])[CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 86754617HCID 86754617, compound

Product 2

HCID 14923Ammonium HydroxideHCID 86754618HCID 86754618, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 0.65 g (1.8 mmol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro-4a-(3-methoxyphenyl)-2-methyl-6-phenyl-6-isoquinolinol in 60 ml of 37% HCl was stirred at room temperature for 90 min. The solution was then concentrated in vacuo up to a volume of ca. 10 ml and the pH was adjusted to 14 with 40% NaOH solution. The aqueous phase was extracted with AcOEt, 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 90:7:0.7 respectively, yielding 0.3 g of the title compound.

Workup

  1. concentrationThe solution was then concentrated in vacuo up to a volume of ca. 10 ml
  2. extractionThe aqueous phase was extracted with AcOEt
  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

Sources & evidence

ORD record
ord-e8731ed2fda446aaa59c1c26a2213f07
Source dataset
uspto-grants-1999_10
Patent number
US05968949

Reaction notes

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