1,2-Diaminocyclohexane, (+)- → HCID 59025424, compound

HRID 2421049Notes

Reaction equation

HRID 2421049 reaction equation
[C@H:1]1([NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[NH2:7].O=[C:10]1[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+].C(=O)([O-])O.[Na+]>ClCCl>[NH2:7][C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@@H:1]1[NH:8][CH:10]1[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

Participants

6

Reactant 4

HCID 4793071,2-Diaminocyclohexane, (+)-HCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59025424HCID 59025424, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1S,2S)-cyclohexane-1,2-diamine (4 g, 35.08 mmol) in dichloromethane (80 mL) was added tert-butyl 4-oxopiperidine-1-carboxylate (3.49 g, 17.54 mmol) followed by sodium triacetoxy borohydride (11.15 g, 52.60 mmol) and stirred at room temperature for 5 hours. A saturated solution of sodium hydrogen carbonate (10 mL) was then added and the reaction diluted in dichloromethane (100 mL). The phases were separated and aqueous phase was extracted with dichloromethane (2×60 mL). Combined organic layers was washed with brine, dried and concentrated in vacuo. The crude compound was purified by flash chromatography to provide the titled compound as yellow oil (3.5 g).

Workup

  1. customThe phases were separated
  2. extractionaqueous phase was extracted with dichloromethane (2×60 mL)
  3. washCombined organic layers was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe crude compound was purified by flash chromatography

Sources & evidence

ORD record
ord-be9a52bbe7034ddebdfd700a647851d9
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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