Dimethyl Sulfate → N-Boc-2-Methyl-Piperidine

HRID 840680

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HRID 840680 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:14]N(CCN(C)C)C.[Li]C(CC)C.S(OC)(OC)(=O)=O>CCOCC.O>[C:1]([N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH3:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

7

반응물 4

HCID 6497Dimethyl SulfateHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 7010304N-(tert-butoxycarbonyl)piperidineHCID 178418400CID 53628100

생성물 1

HCID 4578077N-Boc-2-Methyl-Piperidine수율 99.2%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

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온도
-78 °C

실험 절차

A solution of N-Boc-Piperidine (15.0 g, 80.95 mmol) in ether (160 mL) was cooled to −78° C. and treated with TMEDA (15.9 mL, 105.2 mmol) followed by sec-BuLi (85 mL, 105.2 mmol) dropwise. The mixture was stirred for 3 h at −78° C. and then treated with a solution of dimethyl sulfate (15.3 mL, 161.9 mmol) in 65 mL of ether. The mixture was warmed to room temperature and then was diluted with water and extracted with ether. The combined extracts were dried over K2CO3 and then concentrated to give a crude product as a colorless oil. The product was purified by column chromatography on silca gel with 5% EtOAc/hexane to afford 16.0 g (81%) of product as a clear oil which was homogeneous by TLC analysis. 1H NMR (300 MHz) 67 4.33 (m, 1 H), 3.92-3.81 (pair of br. d, 1 H), 2.81-2.72 (dt, 1H), 1.60-1.36 (m, 15 H), 1.09-1.07 (d, 3 H); 13C NMR (75 MHz) 154.9 (s), 78.6 (s), 45.9 (s), 38.6 (s), 29.9 (s), 28.4 (s), 25.6 (s), 18.6 (s), 15.6 (s), ppm.

후처리

  1. temperatureThe mixture was warmed to room temperature
  2. extractionextracted with ether
  3. dry with materialThe combined extracts were dried over K2CO3
  4. concentrationconcentrated
  5. customto give a crude product as a colorless oil
  6. customThe product was purified by column chromatography on silca gel with 5% EtOAc/hexane

출처 및 근거

ORD 기록
ord-04bcec3d8e0849d38352a346ae5610cd
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369078B1

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