tert-Butyl(2R,5S)-5-azido-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylate → tert-Butyl (2R,5S)-5-amino-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylate

HRID 255349Notes

Reaction equation

HRID 255349 reaction equation
[N:1]([C@@H:4]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:7]([CH2:17][CH2:18][N:19]2[C:24]3[CH:25]=[C:26]([C:29]#[N:30])[CH:27]=[CH:28][C:23]=3[O:22][CH2:21][C:20]2=[O:31])[CH2:6][CH2:5]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[C@@H:7]([CH2:17][CH2:18][N:19]2[C:24]3[CH:25]=[C:26]([C:29]#[N:30])[CH:27]=[CH:28][C:23]=3[O:22][CH2:21][C:20]2=[O:31])[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 86642656tert-Butyl(2R,5S)-5-azido-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylate2×

Product 1

HCID 66774232tert-Butyl (2R,5S)-5-amino-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl (2R,5S)-5-azido-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylate (Intermediate 184, 0.31 g) was hydrogenated in methanol (10 mL) over 10% Pd/C (90 mg) at normal pressure and room temperature overnight. The reaction was degassed, filtered and purified by chromatography on silica gel with a gradient of 0-10% methanol in methylene chloride to give 0.29 g.

Workup

  1. customThe reaction was degassed
  2. filtrationfiltered
  3. custompurified by chromatography on silica gel with a gradient of 0-10% methanol in methylene chloride
  4. customto give 0.29 g

Sources & evidence

ORD record
ord-e48ef4a6f4614951bce8009676018b24
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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