HCID 19995524, compound → HCID 19995517, compound

HRID 2249129Notes

Reaction equation

HRID 2249129 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1[OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Pt]>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:18][CH:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:11][CH:10]1[OH:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 19995524HCID 19995524, compound

Product 1

HCID 19995517HCID 19995517, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3-tert-butoxycarbonylamino-1,2,3,4-tetrahydro-2-naphthalenol (1.05 g) in acetic acid (100 ml) was hydrogenated over platinum oxyde (121 mg) under pressure (5.5.6 bars) at room temperature for 3 days. The catalyst was filtered and the solvent was evaporated under vacuum. The residue was purified by chromatography on silica gel [140 g, elution with ethyl acetate:cyclohexane, 2:8 (0.7 1) and 5:7 (1 1)] to afford the title compound as an oil (915 mg).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was evaporated under vacuum
  3. customThe residue was purified by chromatography on silica gel [140 g, elution with ethyl acetate:cyclohexane, 2:8 (0.7 1) and 5:7 (1 1)]

Sources & evidence

ORD record
ord-20d6be2e7eeb41b69d6343235572fb4c
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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