HCID 15637840, compound → (2R,3R)-3-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 901999Notes

Reaction equation

HRID 901999 reaction equation
[N:1]([C@@H:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[OH:14])=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[OH:14]

Participants

4

Reactant 1

HCID 15637840HCID 15637840, compound

Product 1

HCID 12878373(2R,3R)-3-Amino-1,2,3,4-tetrahydronaphthalen-2-olYield 102%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirring mixture of trans 3-azido-2-hydroxy-1,2,3,4-tetrahydronaphthalene (2.5 g, about 75% pure) dissolved in methanol (132 mL) and 10% palladium on carbon (250 mg) was hydrogenated for 2 h under a hydrogen balloon at room temperature. The reaction mixture was filtered through Celite®, rinsing with methanol, and then evaporated under vacuum to provide the title compound (2.2 g, 72% pure).

Workup

  1. customat room temperature
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washrinsing with methanol
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-891102e495264ec78fd29a8e6276ebc5
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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