Methanol → HCID 68118693, compound

HRID 259020Notes

Reaction equation

HRID 259020 reaction equation
C([O:8][C:9]1[C:10]([CH2:25][OH:26])=[C:11]2[C:16](=[CH:17][CH:18]=1)[C@@H:15]([OH:19])[C@H:14]([NH:20][CH:21]1[CH2:24][CH2:23][CH2:22]1)[CH2:13][CH2:12]2)C1C=CC=CC=1.C[OH:28]>[Pd]>[C:25]([OH:26])(=[O:28])[CH3:10].[CH:21]1([NH:20][C@@H:14]2[CH2:13][CH2:12][C:11]3[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[C:10]=3[CH2:25][OH:26])[C@H:15]2[OH:19])[CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 887MethanolHCID 12393703HCID 12393703, compound

Product 1

HCID 68118693HCID 68118693, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In 20 ml. of methanol is dissolved 300 mg. of trans-6-benzyloxy-2-cyclobutylamino-1-hydroxy-5-hydroxymethyl-1,2,3,4-tetrahydronaphthalene and catalytic reduction is carried out in the presence of 5% palladium-on-carbon as the catalyst. When no more hydrogen is absorbed, the catalyst is filtered off and 60 mg. of acetic acid is added to the filtrate. The mixture is concentrated under reduced pressure and the residue is recrystallized from methanolethyl acetate. The procedure yields trans-2-cyclobutylamino-1,6-dihydroxy-5-hydroxymethyl-1,2,3,4-tetrahydronaphthalene acetate as colorless platelets melting at 143°-145° C (decomp.)

Workup

  1. customWhen no more hydrogen is absorbed
  2. filtrationthe catalyst is filtered off
  3. additionof acetic acid is added to the filtrate
  4. concentrationThe mixture is concentrated under reduced pressure
  5. customthe residue is recrystallized from methanolethyl acetate

Sources & evidence

ORD record
ord-1300e312cce74b78971bd19df5b0700f
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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