Acetone → HCID 12393679, compound

HRID 259016Notes

Reaction equation

HRID 259016 reaction equation
[CH3:1][C:2]([CH3:4])=O.Cl.[NH2:6][C@@H:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:13]=2[C:17]#[N:18])[C@H:8]1[OH:27].[Cl-].[Na+]>CO>[CH2:20]([O:19][C:12]1[C:13]([C:17]#[N:18])=[C:14]2[C:9](=[CH:10][CH:11]=1)[C@@H:8]([OH:27])[C@H:7]([NH:6][CH:2]([CH3:4])[CH3:1])[CH2:16][CH2:15]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5234Sodium ChlorideHCID 12393669HCID 12393669, compound

Product 1

HCID 12393679HCID 12393679, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a mixture of 15 m. acetone and 20 ml. methanol is dissolved 450 mg. of trans-2-amino-6-benzyloxy-5-cyano-1-hydroxy-1,2,3,4-tetrahydronaphthalene hydrochloride and, while nitrogen gas is introduced, 150 mg. of the adduct of lithium cyanoborohydride-dioxane complex is added in small portions at 5°-10° C. After stirring for 2 hours, a saturated aqueous solution of sodium chloride is added and the mixture is extracted with ethyl acetate. The ethyl acetate layers are washed with a saturated aqueous solution of sodium chloride and dried. The solvent is distilled off under reduced pressure and the residue is recrystallized from ethanol-ethyl acetate. The procedure yields white crystals of trans-6-benzyloxy-5-cyano-1-hydroxy-2-isopropylamino-1,2,3,4-tetrahydronaphthalene. This compound is in agreement with the sample according to the prcedure of Example 3. Yield 297 mg.

Workup

  1. additionIn a mixture of 15 m
  2. additionof the adduct of lithium cyanoborohydride-dioxane complex is added in small portions at 5°-10° C
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe ethyl acetate layers are washed with a saturated aqueous solution of sodium chloride
  5. customdried
  6. distillationThe solvent is distilled off under reduced pressure
  7. customthe residue is recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-60c341c428c848b887914e71e306bbd7
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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