Potassium Carbonate → Tert-butyl 7-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

HRID 500496노트

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HRID 500496 반응식
Cl.[CH:2]12[O:10][CH:6]([CH2:7][NH:8][CH2:9]1)[CH2:5][N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]2.C([O-])([O-])=O.[K+].[K+].Cl[CH2:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>CC#N>[CH3:28][C:27]([CH3:30])([CH3:29])[C:26](=[O:31])[CH2:25][N:8]1[CH2:7][CH:6]2[O:10][CH:2]([CH2:3][N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]2)[CH2:9]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 835721-ChloropinacoloneHCID 18540411Tert-butyl 9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate hydrochloride

생성물 1

HCID 18540396Tert-butyl 7-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate수율 85.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
40 °C

실험 절차

A mixture of tert-butyl 9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate hydrochloride (Preparation A; 0.26 g, 1.0 mmol) and K2CO3 (1.45 g, 10.5 mmol) in MeCN (8 mL) was treated with 1-chloropinacolone (0.216 g, 1.6 mmol), and the mixture stirred at 40° C. overnight. The following morning, the temperature was raised to 50° C. for 4 h before the solids were filtered off from the mixture and the filtrate concentrated in vacuo. The crude product was dissolved in DCM and the solution was added to an ion-exchange solid phase extraction plug (10 g CBA (carboxylic acid on silica support)). After 1 h, the plug was washed with DCM (15 mL), after which the product was finally eluted with dichloromethane:MeOH:TEA (90:5:5). The solvents were evaporated to give 0.276 g (85.5%) of the sub-title compound.

후처리

  1. customPreparation A
  2. temperatureThe following morning, the temperature was raised to 50° C. for 4 h before the solids
  3. filtrationwere filtered off from the mixture
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe crude product was dissolved in DCM
  6. additionthe solution was added to an ion-exchange solid phase extraction plug (10 g CBA (carboxylic acid on silica support))
  7. waitAfter 1 h
  8. washthe plug was washed with DCM (15 mL)
  9. washafter which the product was finally eluted with dichloromethane:MeOH:TEA (90:5:5)
  10. customThe solvents were evaporated

출처 및 근거

ORD 기록
ord-cfbe3c24bc4444e2a5a56682062ad052
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772229B2

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