Ethanol → HCID 12393700, compound

HRID 259013Notes

Reaction equation

HRID 259013 reaction equation
C(O)C.[BH4-].[Na+].Cl.[CH2:7]([O:14][C:15]1[C:16]([CH:30]=[O:31])=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[CH:20]([NH:26][CH:27]([CH3:29])[CH3:28])[CH2:19][CH2:18]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[Na+]>C(OCC)(=O)C>[CH2:7]([O:14][C:15]1[C:16]([CH2:30][OH:31])=[C:17]2[C:22](=[CH:23][CH:24]=1)[C@@H:21]([OH:25])[C@H:20]([NH:26][CH:27]([CH3:29])[CH3:28])[CH2:19][CH2:18]2)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 21425557HCID 21425557, compound

Product 1

HCID 12393700HCID 12393700, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In 10 ml. of ethanol is suspended 100 mg. of sodium borohydride and, under stirring, is added 200 mg. of 6-benzyloxy-5-formyl-2-isopropylamino-3,4-dihydro-1(2H)-naphthalenone hydrochloride. The mixture is agitated at room temperature for 2 hours, after which time a saturated solution of sodium chloride and ethyl acetate was added. The ethyl acetate layer is taken, washed with a saturated aqueous solution or sodium chloride and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is recrystallized from ethyl acetate-ethanol. The above procedure provides trans-6-benzyloxy-1-hydroxy-5-hydroxymethyl-2-isopropylamino-1,2,3,4-tetrahydronaphthalene as white crystals. Yield 128 mg.; melting point: 138°-139° C.

Workup

  1. additionis added 200 mg
  2. washwashed with a saturated aqueous solution or sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent is then distilled off under reduced pressure
  5. customthe residue is recrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-a7abdac37be64ef6883f17c26ceaaee9
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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