((R)-4-azido-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester → HCID 59152881, compound

HRID 2387528Notes

Reaction equation

HRID 2387528 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([N:15]=[N+]=[N-])[C:9]=2[CH:8]=[N:7]1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH2:15])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

Participants

4

Reactant 1

HCID 59152877((R)-4-azido-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester

Product 1

HCID 59152881HCID 59152881, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ((R)-4-azido-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester (1.25 g, 5.0 mmol) in ethanol (40 mL) was hydrogenated over 10% Pd/C (130 mg) under 30 psi in a 150 mL Parr bottle at room temperature for 1 hour. The reaction mixture was filtered through a pad of Celite® (diatomite filter). The filtrate was collected and concentrated in vacuo to afford ((R)-4-amino-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester as an oil (1.10 g, 98%), which was used in the next step without further purification. MS calcd. for C11H17N3O2 223, obsd. (ESI+) [(M+H)+] 224.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite® (diatomite filter)
  2. customThe filtrate was collected
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f08fb27d98e147aaac38049707460024
Source dataset
uspto-grants-2012_09
Patent number
US08268870B2

Reaction notes

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