Acetic Acid → HCID 22052529, compound

HRID 1831743Notes

Reaction equation

HRID 1831743 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.CO[C:13]([CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]2[CH:21]3[CH2:30][CH2:29][CH2:28][CH:22]3[C:23](=[O:27])[NH:24][C:25]=2[CH:26]=1)=O.[Cl:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][NH2:36].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.O.C(O)(C)C>[Cl:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][NH:36][CH:16]([C:17]1[CH:18]=[CH:19][C:20]2[CH:21]3[CH2:30][CH2:29][CH2:28][CH:22]3[C:23](=[O:27])[NH:24][C:25]=2[CH:26]=1)[CH2:15][CH3:13]

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 77802Benzenemethanamine, 3-chloro-HCID 5049666Sodium triacetoxyborohydrideHCID 18516355HCID 18516355, compoundHCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 22052529HCID 22052529, compoundYield 41.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.6 ml (1.9 mmol) of 1.2 M diisobutylaluminum hydride (DIBAH) in toluene is added in drops to a solution of 510 mg (1.9 mmol) of 7-(methoxycarbonylethyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 50 ml of toluene at −70° C. After 2 hours at −70° C., the batch is mixed with 0.75 ml (0.9 mmol) of DIBAH solution, stirred for 15 minutes, treated with 3 ml of isopropanol and 1 ml of water and stirred for 2 hours at room temperature. The reaction solution is filtered and concentrated by evaporation in a vacuum. The residue is dissolved in 50 ml of 1,2-dichloroethane, mixed with 0.38 ml (3.1 mmol) of 3-chlorobenzylamine, 0.91 g (4.3 mmol) of sodium (triacetoxy)-borohydride and 0.017 ml (0.29 mmol) of acetic acid and stirred for 24 hours at room temperature. The batch is diluted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with ethyl acetate-methanol yields 290 mg of product.

Workup

  1. stirringstirred for 2 hours at room temperature
  2. filtrationThe reaction solution is filtered
  3. concentrationconcentrated by evaporation in a vacuum
  4. dissolutionThe residue is dissolved in 50 ml of 1,2-dichloroethane
  5. stirringstirred for 24 hours at room temperature
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-7083ef568f1e4a0ead5a57f998ebb1c5
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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