Hydrochloric Acid → HCID 67589431, compound

HRID 863539Notes

Reaction equation

HRID 863539 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][C@H:6]1[CH2:18][CH2:17][N:9]2[C:10]3[C:15]([CH:16]=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)C.[OH-].[Na+].Cl>CO>[CH:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[C:8]1[CH2:7][C@@H:6]([CH2:5][C:4]([OH:19])=[O:3])[CH2:18][CH2:17][N:9]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86752148HCID 86752148, compound

Product 1

HCID 67589431HCID 67589431, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 17 g (63 mmol) of methyl alpha (R or S)-ethyl-6,7,8,9-tetrahydropyrido[1,2-a]indole-8(S)-acetate (diastereomers A+B) in 150 ml of methanol was treated with 130 ml of 2M sodium hydroxide and heated to reflux for 18 hours. The cooled solution was added to 150 ml of 4M hydrochloric acid and the resulting precipitate was filtered off and partitioned between 200 ml of dichloromethane and 100 ml of water. The organic phase was separated, dried over magnesium sulfate and evaporated to give 15 g of alpha (R or S)-6,7,8,9-tetrahydropyrido[1,2-a]indole-8(S)-acetic acid (diastereomers A+B) as a pale pink solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. filtrationthe resulting precipitate was filtered off
  4. custompartitioned between 200 ml of dichloromethane and 100 ml of water
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-84cf276662ae47a8ac27271807bbd30e
Source dataset
uspto-grants-1998_02
Patent number
US05721230

Reaction notes

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