Acetic Acid → HCID 69652723, compound

HRID 1831741Notes

Reaction equation

HRID 1831741 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[CH:8]3[CH2:17][CH2:16][CH2:15][CH:9]3[C:10](=[O:14])[NH:11][C:12]=2[CH:13]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[Cl:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[CH2:44][NH2:45].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl.C(OCC)(=O)C>[Cl:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[CH2:44][NH:45][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[CH:8]3[CH2:17][CH2:16][CH2:15][CH:9]3[C:10](=[O:14])[NH:11][C:12]=2[CH:13]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 77802Benzenemethanamine, 3-chloro-HCID 159087TriacetoxyperiodinaneHCID 5049666Sodium triacetoxyborohydrideHCID 18516364HCID 18516364, compound

Product 1

HCID 69652723HCID 69652723, compoundYield 23.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.19 g (0.82 mmol) of 7-hydroxyethyl-1,2,3,3a,5,9b-hexahydro-cyclopenta[c]quinolin-4-one in 20 ml of dichloromethane is mixed at 0° C. with 0.38 g (0.90 mmol) of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277). The batch is stirred for 10 minutes at 0° C. and for 40 minutes at room temperature, diluted with dichloromethane (100 ml), washed with saturated NaHCO3 (30 ml), dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is dissolved in 1,2-dichloroethane (20 ml) and mixed with 0.11 ml (0.90 mmol) of 3-chlorobenzylamine, 0.30 g (1.40 mmol) of sodium (triacetoxy)borohydride and 0.05 ml (0.85 mmol) of acetic acid. After 20 hours at room temperature, the batch is diluted with ethyl acetate (150 ml), washed with water (2×50 ml), dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with dichloromethane-ethanol yields 69 mg of product.

Workup

  1. washwashed with saturated NaHCO3 (30 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum
  4. dissolutionThe residue is dissolved in 1,2-dichloroethane (20 ml)
  5. waitAfter 20 hours at room temperature
  6. washwashed with water (2×50 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-02925d5ee2bc40bba8c0ba75d5af26c4
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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