Hydrochloric Acid → HCID 20523611, compound

HRID 1703335Notes

Reaction equation

HRID 1703335 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([S:12][CH:13]([CH:15]([CH3:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH3:14])[CH:9]=[C:8]2[C:3]=1[CH:4]1[CH2:26][C:25](=O)[CH2:24][CH2:23][CH:5]1[CH:6]([CH3:22])[NH:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:34].[Na+].Cl>CO>[NH2:34][CH:25]1[CH2:24][CH2:23][CH:5]2[CH:6]([CH3:22])[NH:7][C:8]3[C:3]([CH:4]2[CH2:26]1)=[C:2]([OH:1])[CH:11]=[C:10]([S:12][CH:13]([CH:15]([CH3:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH3:14])[CH:9]=3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 20523607HCID 20523607, compound

Product 1

HCID 20523611HCID 20523611, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml. of dry methanol is added 1.51 g. (3.1 mmole) of dl-1-hydroxy-6-methyl-3-(3-methyl-2-octylthio)-5,6,6a,7,10,10a-hexahydrobenzo[c]quinoline-9(8H)one, 2.39 g. (31 mmole) ammonium acetate and 0.272 g. (4.34 mmole) sodium cyanoborohydride, and the resulting mixture is heated at reflux for two days. The resulting mixture is acidified to pH 2 with hydrochloric acid and evaporated to dryness in vacuo. The residue is taken up in water, washed with ethyl ether, the aqueous phase adjusted to pH 12 with sodium hydroxide solution and extracted with ethyl ether. The extracts are washed with brine, dried over anhydrous magnesium sulfate and evaporated to dryness to provide the title compound as a mixture of diastereomers which are separated, if desired, by fractional crystallization followed by column chromatography on silica gel.

Workup

  1. temperatureat reflux for two days
  2. customevaporated to dryness in vacuo
  3. washwashed with ethyl ether
  4. extractionextracted with ethyl ether
  5. washThe extracts are washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-3a0f11cee823446ab1baf42ef2097011
Source dataset
uspto-grants-1982_09
Patent number
US04351833

Reaction notes

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