(S)-tert-butyl 2-((4-nitro-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate → (S)-tert-butyl 2-((4-amino-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

HRID 522630Notes

Reaction equation

HRID 522630 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][C@H:10]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:8]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][N:7]([CH2:9][C@H:10]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:8]=1

Participants

4

Reactant 1

HCID 118023401(S)-tert-butyl 2-((4-nitro-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

Product 1

HCID 118023185(S)-tert-butyl 2-((4-amino-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (s)-tert-butyl 2-((4-nitro-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate (3.2 g, 10.2 mmol) in methanol (100 mL) was added Pd/C (600 mg). The mixture was stirred under 1 atm H2 at room temperature overnight, and then filtrated through a pad of celite. The filtrate was concentrated to afford (S)-tert-butyl 2-((4-amino-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate. MS (ES+) C13H22N4O3 requires: 282, found: 283 [M+H]+.

Workup

  1. filtrationfiltrated through a pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c30e3bca4e1d43f9b6fac3d092140743
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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