tert-butyl (2R,5S)-2-[(2-aminopyridin-3-yl)ethynyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate → tert-butyl (2R,5S)-2-[2-(2-aminopyridin-3-yl)ethyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate

HRID 629706Notes

Reaction equation

HRID 629706 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[C:9][C@H:10]2[O:15][CH2:14][C@@H:13]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[N:12]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:11]2)=[CH:6][CH:5]=[CH:4][N:3]=1>FC(F)(F)CO.[Pd]>[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][C@H:10]2[O:15][CH2:14][C@@H:13]([CH2:16][O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20])[N:12]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:11]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 86726311tert-butyl (2R,5S)-2-[(2-aminopyridin-3-yl)ethynyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate

Product 1

HCID 86726313tert-butyl (2R,5S)-2-[2-(2-aminopyridin-3-yl)ethyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

To tert-butyl (2R,5S)-2-[(2-aminopyridin-3-yl)ethynyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate (1 eq.) in 2,2,2,-trifluoroethanol (0.4 M) at rt was added 10% Pd/C (0.2 eq.). The reaction was degassed and then shaken under 1 atm of H2 for 24 hrs. The reaction mixture was filtered on celite and concentrated to afford the desired compound.

Workup

  1. customThe reaction was degassed
  2. filtrationThe reaction mixture was filtered on celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-89f2c3218b814a1681e58a1876a17109
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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