1,2-Diaminocyclohexane, (+)- → HCID 57619826, compound

HRID 1642472Notes

Reaction equation

HRID 1642472 reaction equation
[CH3:1][C:2]1([N:15]2[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[C@H:22]1([NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]1[NH2:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCl>[NH2:28][C@H:23]1[CH2:24][CH2:25][CH2:26][CH2:27][C@@H:22]1[NH:29][CH:18]1[CH2:19][CH2:20][N:15]([C:2]2([CH3:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 4793071,2-Diaminocyclohexane, (+)-HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10990126HCID 10990126, compound

Product 1

HCID 57619826HCID 57619826, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-methyl-4-(4-oxo-1-piperidyl)piperidine-1-carboxylate (2.96 g, 10.0 mmol) and (1S,2S)-cyclohexane-1,2-diamine (2.29 g, 20.0 mmol) in dichloromethane (80 mL) was added sodium triacetoxyborohydride (3.18, 15.0 mmol) and stirred at room temperature for 12 h. Saturated NaHCO3 (40 mL) was added, phases were separated and the aqueous layer was extracted with dichloromethane (2×60 mL). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound, which was used for the subsequent step without further purification.

Workup

  1. customphases were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (2×60 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e8b7ad8c7804dfb97139ef0d4258e36
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

Loading…