Acetic Acid → Tert-butyl 4-(3,3-dimethylcyclohexyl)-3-oxopiperazine-1-carboxylate

HRID 2387232Notes

Reaction equation

HRID 2387232 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:14][CH:15]=[O:16])[CH2:9][C:10](OC)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][C:19]1([CH3:26])[CH2:24][CH2:23][CH2:22][CH:21]([NH2:25])[CH2:20]1.CCN(C(C)C)C(C)C.CC(O)=O>CO>[CH3:18][C:19]1([CH3:26])[CH2:24][CH2:23][CH2:22][CH:21]([N:25]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:14][C:15]2=[O:16])[CH2:20]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 671599363,3-dimethylcyclohexan-1-amine hydrochlorideHCID 86646541HCID 86646541, compound

Product 1

HCID 68504448Tert-butyl 4-(3,3-dimethylcyclohexyl)-3-oxopiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (0.19 M) of methyl N-(tert-butoxycarbonyl)-N-(2-oxoethyl)glycinate (prepared as described in Bioorg. Med. Chem. 2007, 15, 2092-2105) in MeOH were added 3,3-dimethylcyclohexanamine hydrochloride (1.5 eq), DIPEA (1.5 eq), NaBH3(CN) (1.5 eq) and AcOH (1.4 eq). After stirring for 2 hours at RT more NaBH3(CN) (1.5 eq) was added and reaction mixture was irradiated at MW for 1 hour at 125° C. MeOH was removed under reduced pressure and the residue purified by filtration on silica with elution of the desired intermediate with EtOAc. Evaporation of the organic solvent yielded tert-butyl 4-(3,3-dimethylcyclohexyl)-3-oxopiperazine-1-carboxylate. MS (ES) C17H30N2O3 requires: 310, found: 311 (M+H)+.

Workup

  1. additionwas added
  2. customreaction mixture
  3. customwas irradiated at MW for 1 hour at 125° C
  4. customMeOH was removed under reduced pressure
  5. filtrationthe residue purified by filtration on silica with elution of the desired intermediate with EtOAc
  6. customEvaporation of the organic solvent

Sources & evidence

ORD record
ord-bd3dc148c47742379c2652fe377716bf
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

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