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

HRID 2387526Notes

Reaction equation

HRID 2387526 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:15]C(OCC3C=CC=CC=3)=O)[C:9]=2[CH:8]=[N:7]1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:26])[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 59152896((R)-4-benzyloxycarbonylamino-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester

Product 1

HCID 59152881HCID 59152881, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ((R)-4-benzyloxycarbonylamino-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester (357 mg, 1.0 mmol) in ethanol was hydrogenolyzed over 10% palladium on carbon (40 mg) under atmospheric pressure at room temperature for 3 hours. The reaction mixture was then 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 (224 mg, 99%) as a light yellow oil. MS calcd. for C11H17N3O2 223, obsd. (ESI+) [(M+H)+] 224.

Workup

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

Sources & evidence

ORD record
ord-7f0946c4bfb94f27be88982983d74c5c
Source dataset
uspto-grants-2012_09
Patent number
US08268870B2

Reaction notes

Loading…