Cyclohexanone, 4,4-dimethyl- → Methyl(2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate

HRID 1361297Notes

Reaction equation

HRID 1361297 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:18][C:19]1([CH3:26])[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1.C([O-])(O)=O.[Na+]>ClCCCl>[CH3:17][O:16][C:14]([C@@H:9]1[CH2:10][C@H:11]([NH:13][CH:22]2[CH2:23][CH2:24][C:19]([CH3:26])([CH3:18])[CH2:20][CH2:21]2)[CH2:12][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])=[O:15]

Participants

5

Reactant 3

HCID 138166Cyclohexanone, 4,4-dimethyl-HCID 516892Sodium BicarbonateHCID 5200425(2S,4S)-1-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

Product 1

HCID 66970872Methyl(2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To methyl (2S,4S)-1-Boc-4-aminopyrrolidine-2-carboxylate (1.07 g, 4.38 mmol) and dimethylcyclohexanone (0.66 g, 5.25 mmol) in DCE (20 mL) was added dropwise NaBH(OAc) (1.39 g, 6.57 mmol) at rt. The reaction mixture was stirred at rt for 4 h, a saturated NaHCO3 aqueous solution was added, and extracted with DCM (50 mL×2) and EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The obtained residue was purified by column chromatography (eluent, EtOAc/Hex=1/2) to give the title compound (1.16 g, 75%).

Workup

  1. extractionextracted with DCM (50 mL×2) and EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by column chromatography (eluent, EtOAc/Hex=1/2)

Sources & evidence

ORD record
ord-0ccbc25c64664fd1a98688cf38a9efac
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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