Cyclohexanone, 4,4-dimethyl- → HCID 66971206, compound

HRID 1361307Notes

Reaction equation

HRID 1361307 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[C:10]([N:17]1[CH2:21][CH2:20][C@H:19]([NH2:22])[CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]>C(Cl)Cl>[C:10]([N:17]1[CH2:21][CH2:20][C@H:19]([NH:22][CH:5]2[CH2:6][CH2:7][C:2]([CH3:9])([CH3:1])[CH2:3][CH2:4]2)[CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 138166Cyclohexanone, 4,4-dimethyl-HCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Product 1

HCID 66971206HCID 66971206, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,4-dimethylcyclohexanone (3.8 g, 30 mmol) in DCM (200 ml) was added commercially obtained (3S)-1-Boc-3-aminopyrrolidine (5.6 g, 30 mmol), and NaBH(OAc) (12.7 g, 60 mmol) was added, and stirred at rt for 6 h. After the reaction finished, the solvent was concentrated in vacuo, a NaHCO3 aqueous solution was added, and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (eluent: EtOAc/Hex=2/1) to give the title compound (8.4 g, 94.5%).

Workup

  1. additionwas added
  2. concentrationthe solvent was concentrated in vacuo
  3. additiona NaHCO3 aqueous solution was added
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (eluent: EtOAc/Hex=2/1)

Sources & evidence

ORD record
ord-41672f21e37e4f178bae5fba2be2fd2d
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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