1,1-Dichloroethane → HCID 86755480, compound

HRID 1421905Notes

Reaction equation

HRID 1421905 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][C@@H:10]3[C@H:14]([CH2:15][C:7]=2[CH:6]=[CH:5][CH:4]=1)[NH:13][CH2:12][CH2:11]3.[C:16]1([C:22]2[CH:35]=[CH:34][C:25]([C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH:32]=O)=[O:27])=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:50]C(Cl)C>>[ClH:50].[CH3:1][O:2][C:3]1[C:8]2[CH2:9][C@@H:10]3[C@H:14]([CH2:15][C:7]=2[CH:6]=[CH:5][CH:4]=1)[N:13]([CH2:32][CH2:31][CH2:30][CH2:29][NH:28][C:26](=[O:27])[C:25]1[CH:34]=[CH:35][C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:23][CH:24]=1)[CH2:12][CH2:11]3

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 10262307HCID 10262307, compoundHCID 217125654-(4-Phenylbenzoylamino)butyraldehyde

Product 1

HCID 86755480HCID 86755480, compoundYield 38%

Procedure

A mixture of cis-2,3,3a,4,9,9a-hexahydro-5-methoxy-1H-benz[f]indole (D17, 0.08 g, 0.39 mmol), 4-(4-phenylbenzoylamino)butyraldehyde (0.11 g, 0.40 mmol), and sodium triacetoxyborohydride (0.13 g, 0.61 mmol) in dichioroethane (20 ml), was stirred at room temperature for 18 h. Resulting mixture was partitioned between saturated aqueous NaHCO3 (20 ml) and dichloromethane (3×10 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography on silica using 0-4% methanol-dichloromethane gradient elution gave the free base of the title compound as a colourless solid (0.07 g, 38%). The free base was treated with 1M ethereal HCl (0.31 ml, 0.3 mmol) in dry dichloromethane to afford after evaporation the title compound.

Workup

  1. customResulting mixture
  2. customwas partitioned between saturated aqueous NaHCO3 (20 ml) and dichloromethane (3×10 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give an oil
  6. washChromatography on silica using 0-4% methanol-dichloromethane gradient elution

Sources & evidence

ORD record
ord-54b28631b19e4a6790d33bbf135ad87a
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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