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

HRID 898791ノート

反応式

HRID 898791 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d09efe7ce2654d44ba9bcd56e0b01d37
出典データセット
uspto-grants-2008_04
特許番号
US07351821B2

反応ノート

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