Formaldehyde → (+/-)-cis-N1-Benzyl-N2-tert-butoxycarbonyl-N1-methyl-1,2-cyclohexanediamine

HRID 546421Notes

Reaction equation

HRID 546421 reaction equation
[CH2:1]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:25]([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO>[CH2:1]([N:8]([CH3:25])[C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 58822072(+/-)-cis-N1-Benzyl-N 2-tert-butoxycarbonyl-1,2-cyclohexanediamine

Product 1

HCID 58822120(+/-)-cis-N1-Benzyl-N2-tert-butoxycarbonyl-N1-methyl-1,2-cyclohexanediamineYield 58.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-cis-N1-Benzyl-N2-tert-butoxycarbonyl-1,2-cyclohexanediamine (3.24 g) was dissolved in methanol (30 ml), and to the solution an aqueous solution (35%, 0.909 ml) of formaldehyde was added, and the mixture was stirred at room temperature for 10 minutes. Sodium cyanoborohydride (666 mg) was added to this mixture, and the resultant mixture was stirred at room temperature for 6 hours. Thereafter, a saturated aqueous solution of sodium hydrogencarbonate was added, and the solvent was concentrated under reduced pressure. Dichloromethane was added to the residue to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=3:1) to obtain the title compound (1.98 g) as a yellow oil.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure
  2. additionDichloromethane was added to the residue
  3. customto separate an organic layer
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-ef61c25e02c34fcdac7b888704eb228a
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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