2-Indanone → HCID 54345220, compound

HRID 1952966Notes

Reaction equation

HRID 1952966 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].[CH2:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C:11]1=O.C([BH3-])#N.[Na+]>C(O)C.CO>[OH:8][CH2:7][C@H:5]([NH:6][CH:11]1[CH2:10][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)[C:4]([O:3][CH3:2])=[O:9]

Participants

6

Reactant 3

HCID 119832-IndanoneHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydride

Product 1

HCID 54345220HCID 54345220, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

L-serine methyl ester hydrochloride (0.05 moles, 7.78 g) is dissolved in absolute ethanol (400 ml) and methanol (40 ml), added with 2-indanone (0.05 moles, 6.74 g) and sodium cyanoborohydride (0.55 moles, 3.64 g) under stirring in 30 minutes. The mixture is stirred at r.t. for 5 hours, then evaporated to dryness under vacuum and the residue is taken up into water (150 ml) and ethyl acetate (150 ml). The phases are separated and the aqueous phase is further extracted with ethyl acetate (200 ml). The combined organic phases are extracted with a 0.2 N HCl solution (2×200 ml). The aqueous solution is separated, adjusted to pH=8 with sodium bicarbonate and extracted with ethyl acetate (2×300 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: 8.4 g (71.4%)

Workup

  1. stirringThe mixture is stirred at r.t. for 5 hours
  2. customevaporated to dryness under vacuum
  3. customThe phases are separated
  4. extractionthe aqueous phase is further extracted with ethyl acetate (200 ml)
  5. extractionThe combined organic phases are extracted with a 0.2 N HCl solution (2×200 ml)
  6. customThe aqueous solution is separated
  7. extractionextracted with ethyl acetate (2×300 ml)
  8. customThe organic solution is separated
  9. dry with materialdried over sodium sulfate
  10. customevaporated under vacuum
  11. customThe resulting product is dried under vacuum at r.t

Sources & evidence

ORD record
ord-19a74870c11a4be99225f1666b89548e
Source dataset
uspto-grants-2000_09
Patent number
US06114391

Reaction notes

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