Propionic Acid → 1-(2,8-Dimethyl-1-thia-3,8-diaza-spiro[4.5]dec-3-yl)-propan-1-one

HRID 574625노트

반응식

HRID 574625 반응식
[CH3:1][CH:2]1[NH:6][CH2:5][C:4]2([CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)[S:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[C:28](O)(=[O:31])[CH2:29][CH3:30]>ClCCl>[CH3:1][CH:2]1[N:6]([C:28](=[O:31])[CH2:29][CH3:30])[CH2:5][C:4]2([CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)[S:3]1

참가 물질

5

반응물 3

HCID 1032Propionic AcidHCID 10868DicyclohexylcarbodiimideHCID 669939622,8-Dimethyl-1-thia-3,8-diazaspiro[4.5]decane

생성물 1

HCID 468468051-(2,8-Dimethyl-1-thia-3,8-diaza-spiro[4.5]dec-3-yl)-propan-1-one수율 44.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2,8-dimethyl-1-thia-3,8-diaza-spiro[4.5]decane (Example 1) (0.86 g, 4.62 mmol) in dichloromethane (90 ml) at room temperature was added dicyclohexylcarbodiimide (DCC) (1.28 g, 6.2 mmol) followed by addition of propionic acid (0.41 ml, 5.5 mmol). The resulting solution was stirred at room temperature overnight. During the reaction a white solid precipitated. After filtration the solvent was evaporated and the crude product was purified by flash chromatography (silica, CH2Cl2/MeOH/NH4OH 90/10/1) to give the title compound (0.5 g) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 5.51, 5.19 (2q, J=6.15 and J=6.22 Hz, 1H, CHCH3), 4.63, 3.74 (2d, J=11.88 and J=11.57 Hz, 1H, CHHNCO), 3.44, 3.08 (2d, J=11.55 and J=12.09 Hz, 1H, CHHNCO), 2.8-2.6 (m, 2H), 2.5-2.2 (m, 7H, CH2, CH2CH3, NCH3), 2.2-2.0 (m, 1H), 2.0-1.8 (m, 3H) 1.52, 1.48 (2d, J=6.30 and J=6.18 Hz, 3H, CH3—CH), 1.19-1.12 (m, 3H, CH3) ppm; 13C NMR (CDCl3, 300 MHz) δ 171.6 (C), 57.5, 57.2 (CH), 55.5 (C), 54.7, 54.3 (CH2), 53.2, 53.0 (CH2), 46.3 (CH3), 38.4, 37.7 (CH2), 37.0, 36.4 (CH2), 28.8, 26.8 (CH2), 25.6, 23.6 (CH3), 9.6, 9.4 (CH3) ppm.

후처리

  1. customDuring the reaction a white solid
  2. customprecipitated
  3. filtrationAfter filtration the solvent
  4. customwas evaporated
  5. customthe crude product was purified by flash chromatography (silica, CH2Cl2/MeOH/NH4OH 90/10/1)

출처 및 근거

ORD 기록
ord-7784dd8a4e204aafb18b04ab26a613b3
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034891B2

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