(S)-2-Azido-indan-1-ol → (S)-2-Amino-indan-1-ol

HRID 885408Notes

Reaction equation

HRID 885408 reaction equation
[N:1]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@@H:5]1[OH:13])=[N+]=[N-]>CCO.[Pd]>[NH2:1][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@@H:5]1[OH:13]

Participants

4

Reactant 1

HCID 58237515(S)-2-Azido-indan-1-ol

Product 1

HCID 53893097(S)-2-Amino-indan-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To (S)-2-azido-indan-1-ol (9.39 mmol) in EtOH (45 mL) was added 10% palladium on carbon (0.20 g), and the mixture was stilled under H2 using a Parr apparatus for 4 hours. Analytical LCMS indicated that some starting material was still present, so additional 10% palladium on carbon (0.20 g) was added, and the reaction was stirred overnight under H2 using a Parr apparatus. The mixture was filtered over a pad of Celite and rinsed well with EtOH. The filtrate was concentrated to give the title compound.

Workup

  1. customfor 4 hours
  2. filtrationThe mixture was filtered over a pad of Celite
  3. washrinsed well with EtOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-435314ee9fc94b499a6ddb7ce971ead5
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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