Tetrahydro-4H-pyran-4-one → tert-butyl N-[1-(oxan-4-yl)piperidin-4-yl]carbamate

HRID 574762

반응식

HRID 574762 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[O:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[O:15]1[CH2:20][CH2:19][CH:18]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)[CH2:17][CH2:16]1

참가 물질

5

반응물 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 45792109tert-butyl N-[1-(oxan-4-yl)piperidin-4-yl]carbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Tert-butyl piperidin-4-ylcarbamate (45.00 g, 225 mmol) and dihydro-2H-pyran-4(3H)-one (24.74 g, 247 mmol) were added to dichloromethane (1000 mL). Sodium triacetoxyborohydride (61.90 g, 292 mmol) was added, and the solution was stirred at room temperature for 16 hours. The solution was extracted with 1M sodium hydroxide and dried over anhydrous sodium sulfate. The solution was filtered and concentrated and purified by flash column chromatography on silica gel with 10% methanol (in dichloromethane) increasing to 20% methanol (in dichloromethane).

후처리

  1. extractionThe solution was extracted with 1M sodium hydroxide
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography on silica gel with 10% methanol (in dichloromethane)
  6. temperatureincreasing to 20% methanol (in dichloromethane)

출처 및 근거

ORD 기록
ord-0000bc7bfcdc4a1d93c74d3f4c9336b4
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034875B2

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