2-Indanone → HCID 23302032, compound

HRID 1952964Notes

Reaction equation

HRID 1952964 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4][NH2:5].[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C:8]1=O.C([BH3-])#N.[Na+]>C(O)C.CO>[CH:7]1([NH:5][CH2:4][C:3]([O:2][CH3:1])=[O:6])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 119832-IndanoneHCID 69221Glycine methyl esterHCID 5003444Sodium cyanoborohydride

Product 1

HCID 23302032HCID 23302032, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Glycine methyl ester (0.053 moles, 6.64 g) is dissolved in absolute ethanol (420 ml) and methanol (42 ml), added with 2-indanone (0.053 moles, 7 g), and with sodium cyanoborohydride (0.058 moles, 3.7 g) under stirring, in 40 minutes. The mixture is left under stirring at r.t. overnight, evaporated to dryness under vacuum and the residue is taken up with water (500 ml) and ethyl acetate (500 ml). The phases are separated and the organic phase is extracted with a 0.1N HCl solution (3×200 ml). The acidic solution is adjusted to pH 8.5-9 with a sodium bicarbonate saturated solution and 20 extracted with ethyl acetate (3×250 ml). The organic solution is separated, dried over sodium sulfate and evaporated under vacuum. The resulting product is dried under vacuum at r.t. Yield: 5.8 g (53.4%)

Workup

  1. waitThe mixture is left
  2. customevaporated to dryness under vacuum
  3. customThe phases are separated
  4. extractionthe organic phase is extracted with a 0.1N HCl solution (3×200 ml)
  5. extractionextracted with ethyl acetate (3×250 ml)
  6. customThe organic solution is separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated under vacuum
  9. customThe resulting product is dried under vacuum at r.t

Sources & evidence

ORD record
ord-8cdeadf583984f50936d362dce4a1ce2
Source dataset
uspto-grants-2000_09
Patent number
US06114391

Reaction notes

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