benzyl ((1S,3R)-3-(pyrazin-2-ylamino)cyclohexyl)carbamate → (1R,3S)-N1-(pyrazin-2-yl)cyclohexane-1,3-diamine

HRID 527092Notes

Reaction equation

HRID 527092 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14]C(=O)OCC2C=CC=CC=2)[CH2:9]1>CO.[Pd]>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([NH2:14])[CH2:9]1

Participants

4

Reactant 1

HCID 68007319benzyl ((1S,3R)-3-(pyrazin-2-ylamino)cyclohexyl)carbamate

Product 1

HCID 68007257(1R,3S)-N1-(pyrazin-2-yl)cyclohexane-1,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl N-[(1S,3R)-3-(pyrazin-2-ylamino)cyclohexyl]carbamate, 74a, (0.040 g, 0.123 mmol) in methanol (10 mL) was added 10% Pd/C (0.043 g, 0.040 mmol) and the resulting suspension was stirred under an atmosphere of hydrogen for three hours until LCMS indicated completion of the reaction. The solution was filtered through a bed of celite and concentrated in vacuo to give a yellow solid, which was used without further purification.

Workup

  1. customcompletion of the reaction
  2. filtrationThe solution was filtered through a bed of celite and
  3. concentrationconcentrated in vacuo
  4. customto give a yellow solid, which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-975e89312cda47f3b7a3bdaae97435c5
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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