HCID 59344936, compound → HCID 59344946, compound

HRID 19205Notes

Reaction equation

HRID 19205 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][C@H:8]1[CH2:13][C@@H:12]([CH2:14][N:15]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[N:16]2)[O:11][C:10]([CH3:24])([CH3:23])[O:9]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:25])[CH2:7][C@H:8]1[CH2:13][C@@H:12]([CH2:14][N:15]2[CH:19]=[CH:18][C:17]([NH2:20])=[N:16]2)[O:11][C:10]([CH3:24])([CH3:23])[O:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 59344936HCID 59344936, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59344946HCID 59344946, compoundYield 117%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of [(4R,6S)-2,2-dimethyl-6-(3-nitro-pyrazol-1-ylmethyl)-[1,3]dioxan-4-yl]-acetic acid t-butyl ester (1.56 g 3.52 mmol) in ethanol (25 mL) was hydrogenated in a Parr hydrogenator at 50 psi hydrogen pressure, using 10% palladium on carbon (0.2 g, 0.19 mmol), for 3 h. The reaction mixture was filtered through a celite plug, and the filtrate concentrated which afforded [(4R,6S)-6-(3-amino-pyrazol-1-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid t-butyl ester (1.34 g, 94%) as a yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through a celite plug
  2. concentrationthe filtrate concentrated which

Sources & evidence

ORD record
ord-d4f841ea918444cd941937dd7d8120e7
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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