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

HRID 1361297노트

반응식

HRID 1361297 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-0ccbc25c64664fd1a98688cf38a9efac
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879852B2

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