1,2-Diaminocyclohexane, cis- → HCID 66757269, compound

HRID 1642489Notes

Reaction equation

HRID 1642489 reaction equation
[C@@H:1]1([NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[NH2:7].[CH3:9][C:10]1([N:23]2[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]2)[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[NH2:7][C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:1]1[NH:8][CH:26]1[CH2:25][CH2:24][N:23]([C:10]2([CH3:9])[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 3429171,2-Diaminocyclohexane, cis-HCID 5049666Sodium triacetoxyborohydrideHCID 10990126HCID 10990126, compound

Product 1

HCID 66757269HCID 66757269, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cis-cyclohexane-1,2-diamine (0.850 mL, 7.22 mmol) in dichloromethane (10 mL) was added with tert-butyl 4-methyl-4-(4-oxo-1-piperidyl)piperidine-1-carboxylate (1.39 g, 3.61 mmol) in dichloromethane (5 mL) followed by sodium triacetoxyborohydride (0.918 g, 4.33 mmol) and the mixture stirred at room temperature over night. The mixture was then quenched with 1 N NaOH and dichloromethane was added. The phases were separated and aqueous phase was extracted with dichloromethane. The combined organic phases were dried and concentrated in vacuo to give the title product, which was used for the subsequent step without further purification. MS (M+1): 395.37.

Workup

  1. customThe mixture was then quenched with 1 N NaOH and dichloromethane
  2. additionwas added
  3. customThe phases were separated
  4. extractionaqueous phase was extracted with dichloromethane
  5. customThe combined organic phases were dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9683303a190b424db3f802e4c9a8a5b2
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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