1-Phenethylamine, (-)- → HCID 22850694, compound

HRID 486780Notes

Reaction equation

HRID 486780 reaction equation
CS(O[CH2:6][C@@H:7]1[CH2:19][N:11]2[C:12]3[C:17]([CH:18]=[C:10]2[CH2:9][C@H:8]1[CH2:20]OS(C)(=O)=O)=[CH:16][CH:15]=[CH:14][CH:13]=3)(=O)=O.[CH3:26][C@H:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(O)C>[CH3:26][C@H:27]([N:34]1[CH2:6][C@@H:7]2[C@H:8]([CH2:9][C:10]3[N:11]([CH2:19]2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[CH:18]=3)[CH2:20]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 86747651HCID 86747651, compound

Product 1

HCID 22850694HCID 22850694, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 11.0 g of trans-6,7,8,9-tetrahydro-7,8-bis[(methanesulphonyloxy)methyl]pyrido[1,2-a]indole [prepared as described in Example 14(iv)] in 60 ml of ethanol was treated with 26 ml of (S)-α-methylbenzylamine and heated to reflux for 18 hours. The cooled solution was concentrated and the precipitate was filtered off and purified by chromatography on silica gel using ethyl acetate/petroleum ether (2:1) for the elution. There were obtained 2.1 g of trans-2,3,3a,4,11,11a-hexahydro-2-[alpha(S)-methylbenzyl]-1H-pyrrolo[3',4':4,5]pyrido[1,2-a]indole, diastereomer A, of melting point 153° C., [α]D20 =+17.7° (CHCl3, c=0.51), and 1.6 g of trans-2,3,3a,4,11,11a-hexahydro-2-[alpha(S)-methylbenzyl]-1H-pyrrolo[3',4':4,5]pyrido[1,2-a]indole, diastereomer B, of melting point 154°-156° C.; [α]D20 =-54.2° (CHCl3, c=0.49).

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. concentrationThe cooled solution was concentrated
  4. filtrationthe precipitate was filtered off
  5. custompurified by chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-81d594250d3e4e7bb4fc12fc65acd680
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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