Acetone → HCID 12393672, compound

HRID 259018Notes

Reaction equation

HRID 259018 reaction equation
[NH2:1][C@@H:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8]=2[C:12]([O:14][CH3:15])=[O:13])[C@H:3]1[OH:24].[CH3:25][C:26]([CH3:28])=O>C1C=CC=CC=1>[CH2:17]([O:16][C:7]1[C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:9]2[C:4](=[CH:5][CH:6]=1)[C@@H:3]([OH:24])[C@H:2]([NH:1][CH:26]([CH3:28])[CH3:25])[CH2:11][CH2:10]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 12393665HCID 12393665, compound

Product 1

HCID 12393672HCID 12393672, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

500 mg. of trans-2-amino-6-benzyloxy-1hydroxy-5-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene is dissolved in a mixture of 3 ml. of acetone and 10 ml. of anhydrous benzene and the solution is heated on reflux for 5 hours. The reaction mixture is concentrated under reduced pressure and 10 ml. of ethanol is added to the residue. After the addition of 100 mg. of sodium borohydride with stirring, the mixture is stirred at room temperature for 5 hours. The reaction mixture is concentrated under reduced pressure, and water and ethyl acetate are added to the residue. The mixture is extracted with ethyl acetate. The organic solvent layers are pooled, washed with water, dried and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate-n-hexane to obtain trans-6-benzyloxy-2isopropylamino-1-hydroxy-5-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene as colorless needles melting at 91°-92° C.

Workup

  1. temperatureon reflux for 5 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure and 10 ml
  3. additionof ethanol is added to the residue
  4. additionAfter the addition of 100 mg
  5. stirringthe mixture is stirred at room temperature for 5 hours
  6. concentrationThe reaction mixture is concentrated under reduced pressure, and water and ethyl acetate
  7. additionare added to the residue
  8. extractionThe mixture is extracted with ethyl acetate
  9. washwashed with water
  10. customdried
  11. concentrationconcentrated under reduced pressure
  12. customThe residue is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-5a055605504d47229acaec10b88e7c2f
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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