Hydrochloric Acid → HCID 10104276, compound

HRID 1609391Notes

Reaction equation

HRID 1609391 reaction equation
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][C@@H:12]([C:14](OC3(C)CCC(C(C)C)CC3)=[O:15])[CH2:11][CH2:10][N:5]12.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>O1CCCC1.O>[OH:15][CH2:14][C@H:12]1[CH2:11][CH2:10][N:5]2[C:6]3[C:2]([CH:3]=[C:4]2[CH2:13]1)=[CH:1][CH:9]=[CH:8][CH:7]=3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 67589174HCID 67589174, compound

Product 1

HCID 10104276HCID 10104276, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.8 g (2.27 mmol) of 1-menthyl 6,7,8,9tetrahydropyrido[1,2-a]indole-8(S)-carboxylate in 15 ml of dry tetrahydrofuran was treated dropwise under a nitrogen atmosphere with 2 ml (2 mmol) of 1M lithium aluminum hydride. After 10 minutes, the mixture was cooled in ice, treated successively with 5 ml of ethyl acetate and 30 ml of water and acidified with 1M hydrochloric acid. The mixture was extracted three times with diethyl ether and the combined extracts were dried over sodium sulfate and evaporated. Flash chromatography on silica gel using ethyl acetate/hexane (1:1) for the elution gave (S)-8-(hydroxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indole as a white solid which was dissolved in 5 ml of dichloromethane. Then, 0.43 g (4.21 mmol) of acetic anhydride and 0.9 ml (6.5 mmol) of triethylamine were added and the solution was left to stand for 17 hours. The solvent was evaporated. The residue was partitioned between 5% aqueous sodium bicarbonate solution and diethyl ether. The organic phase was dried over sodium sulfate and evaporated. The residue was crystallized from aqueous ethanol to give 0.518 g (94%) of (S)-8-(acetoxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indole as a white solid of melting point 63°-64° C.; [α]589 ;20 =43.7° (c=1% in chloroform).

Workup

  1. temperaturethe mixture was cooled in ice
  2. extractionThe mixture was extracted three times with diethyl ether
  3. dry with materialthe combined extracts were dried over sodium sulfate
  4. customevaporated
  5. washfor the elution

Sources & evidence

ORD record
ord-816a146de71441e293ef6ea8d5235e95
Source dataset
uspto-grants-1995_03
Patent number
US05399712

Reaction notes

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