(2S,4R)-tert-butyl 2-(azidomethyl)-4-(5-cyclopropylpyrazin-2-yloxy)-pyrrolidine-1-carboxylate → (2S,4R)-tert-butyl 2-(aminomethyl)-4-(5-cyclopropylpyrazin-2-yloxy)-pyrrolidine-1-carboxylate

HRID 1184606Notes

Reaction equation

HRID 1184606 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][C@@H:8]([O:10][C:11]2[CH:16]=[N:15][C:14]([CH:17]3[CH2:19][CH2:18]3)=[CH:13][N:12]=2)[CH2:7][N:6]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N+]=[N-]>N.CO.[Ni]>[NH2:1][CH2:4][C@@H:5]1[CH2:9][C@@H:8]([O:10][C:11]2[CH:16]=[N:15][C:14]([CH:17]3[CH2:18][CH2:19]3)=[CH:13][N:12]=2)[CH2:7][N:6]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

Participants

4

Reactant 1

HCID 86680519(2S,4R)-tert-butyl 2-(azidomethyl)-4-(5-cyclopropylpyrazin-2-yloxy)-pyrrolidine-1-carboxylate

Product 1

HCID 86680520(2S,4R)-tert-butyl 2-(aminomethyl)-4-(5-cyclopropylpyrazin-2-yloxy)-pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

The product from Example 174C (2.54 g, 7.05 mmol) in 7 M ammonia-methanol (30 mL) was added to Raney®-nickel 2800 water slurry (2.54 g, 43.3 mmol; washed once with methanol) in a 250 mL stainless steel pressure bottle. The mixture was shaken under 30 psi of hydrogen at room temperature for 4 hours with periodic venting of nitrogen gas. The mixture was filtered through a 0.45 micron nylon filter, and the volatiles were removed in vacuo to give the title compound.

Workup

  1. washwashed once with methanol) in a 250 mL stainless steel pressure bottle
  2. filtrationThe mixture was filtered through a 0.45 micron nylon
  3. filtrationfilter
  4. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-5dd067c390ee41b5b4fa9132c88201dc
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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