Potassium Hydroxide → HCID 70417581, compound

HRID 2231292Notes

Reaction equation

HRID 2231292 reaction equation
C[O:2][C:3](=[O:26])[CH:4]([C@@:6]1([CH2:24][CH3:25])[C@@H:15]2[N:10]([CH2:11][CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH3:23])[C:14]=32)[CH2:9][CH2:8][CH2:7]1)[CH3:5].[OH-].[K+]>C(O)C>[CH2:24]([C@:6]1([CH:4]([CH3:5])[C:3]([OH:26])=[O:2])[C@@H:15]2[N:10]([CH2:11][CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH3:23])[C:14]=32)[CH2:9][CH2:8][CH2:7]1)[CH3:25]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 70417302HCID 70417302, compound

Product 1

HCID 70417581HCID 70417581, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The solution of 10.0 g. (0.028 moles) of (-)-(1S,12bS)-1-ethyl-12-methyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-1-yl-propionic acid methyl ester (prepared as described in Example 48) in 200 ml. of 96% of ethanol containing 2.5 g. (0.044 moles) of potassium hydroxide is refluxed for one hour. After cooling down, the solution is evaporated to dryness, the evaporation residue is dissolved in a little amount of water and acidified to pH 6 by adding acetic acid. The precipitated product is filtered, washed with water and dried to give 6.28 g. (66.0% yield) of the title compound with an Rf value of 0.51 (Polygram SIL G/UV254 ; developed by an 5:1 mixture of isopropanol with 25% aqueous ammonia solution; detected by UV light).

Workup

  1. temperatureAfter cooling down
  2. customthe solution is evaporated to dryness
  3. dissolutionthe evaporation residue is dissolved in a little amount of water
  4. additionby adding acetic acid
  5. filtrationThe precipitated product is filtered
  6. washwashed with water
  7. customdried
  8. customto give 6.28 g

Sources & evidence

ORD record
ord-e1a56d402efa4a02882cdfbddc49068e
Source dataset
uspto-grants-1988_11
Patent number
US04782052

Reaction notes

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