1,2-Diaminocyclohexane, (+)- → ethyl 4-[4-[[(1S,2S)-2-aminocyclohexyl]amino]-1-piperidyl]-4-methyl-piperidine-1-carboxylate

HRID 1642467Notes

Reaction equation

HRID 1642467 reaction equation
[CH3:1][C:2]1([N:13]2[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[C@H:20]1([NH2:27])[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]1[NH2:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCl>[NH2:26][C@H:21]1[CH2:22][CH2:23][CH2:24][CH2:25][C@@H:20]1[NH:27][CH:16]1[CH2:17][CH2:18][N:13]([C:2]2([CH3:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 4793071,2-Diaminocyclohexane, (+)-HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57619824Ethyl 4-methyl-4-(4-oxo-1-piperidyl)piperidine-1-carboxylate

Product 1

HCID 44541147ethyl 4-[4-[[(1S,2S)-2-aminocyclohexyl]amino]-1-piperidyl]-4-methyl-piperidine-1-carboxylateYield 47.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution ethyl 4-methyl-4-(4-oxo-1-piperidyl)piperidine-1-carboxylate (336 mg, 1.25 mmol) and (1S,2S)-cyclohexane-1,2-diamine (286 mg, 0.5 mmol) in dichloromethane (10 mL) was added sodium triacetoxyborohydride (398 mg, 1.88 mmol) and stirred at room temperature for 12 h. Saturated NaHCO3 (5 mL) was added, the phases were separated and the aqueous phase was extracted with dichloromethane (2×10 mL). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by passing through a short silica gel pad (5-10% MeOH in dichloromethane) to afford the title compound (87 mg, 19%). MS (M+1): 367.31.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane (2×10 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-1b97ca16fe42434790770a17b98194ed
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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