1,2-Diaminocyclohexane, trans- → HCID 57619817, compound

HRID 1642476Notes

Reaction equation

HRID 1642476 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 438061,2-Diaminocyclohexane, trans-HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10990126HCID 10990126, compound

Product 1

HCID 57619817HCID 57619817, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-methyl-4-(4-oxo-1-piperidyl)piperidine-1-carboxylate (2.0 g, 6.76 mmol) and (1R,2R)-cyclohexane-1,2-diamine (1.55 g, 13.5 mmol) in dichloromethane (60 mL) was added sodium triacetoxyborohydride (2.12 g, 10.0 mmol) and stirred at room temperature for 12 h. Saturated NaHCO3 (40 mL) was added, the phases were separated and the aqueous phase was extracted with dichloromethane (2×60 mL). The combined organic phases were washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude product was used for the next step without further purification.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase 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
  6. customThe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-b174e1de3a2044639b42de3f1bc72753
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

Loading…