Water → rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-propionyl-1H-benzo[e]indole

HRID 1109210Notes

Reaction equation

HRID 1109210 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][NH:11]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:26])[CH2:24][CH3:25].O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[C:23](=[O:26])[CH2:24][CH3:25])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 101650127rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

Product 1

HCID 131718473rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-propionyl-1H-benzo[e]indoleYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.35 g (0.0116 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 40 ml of CH2Cl2, 2.80 ml (0.0201 mol) of triethylamine were added thereto and a solution of 1.1 ml (0.0127 mol) of propionyl chloride in 10 ml of CH2Cl2 was added dropwise thereto at 25° under argon. The mixture was stirred at room temperature for 1 hour, then poured into water and extracted with CH2Cl2. The organic phase was dried with MgSO4, filtered and concentrated. By chromatography of the residue over silica gel with ether/ethyl acetate 1:1 there were obtained 3.0 g (99.7%) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-propionyl-1H-benzo[e]indole as a pale yellow, oily material which crystallized overnight; m.p. 81°.

Workup

  1. customat 25°
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic phase was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-63d5646dd8ab45e087bcf16b6dcf2670
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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