Acetaldehyde → 2,8-Dimethyl-1-oxa-3,8-diazaspiro[4.5]decane

HRID 574619

반응식

HRID 574619 반응식
[NH2:1][CH2:2][C:3]1([OH:10])[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.S([O-])([O-])(=O)=O.[Mg+2].[CH:17](=O)[CH3:18]>ClCCl>[CH3:17][CH:18]1[NH:1][CH2:2][C:3]2([CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]2)[O:10]1

참가 물질

5

반응물 3

HCID 177AcetaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 64842624-(Aminomethyl)-1-methylpiperidin-4-ol

생성물 1

HCID 197553342,8-Dimethyl-1-oxa-3,8-diazaspiro[4.5]decane수율 85.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 4-aminomethyl-1-methyl-piperidin-4-ol (2.127 g, 14.77 mmol) in dichloromethane (15 ml) was added anhydrous magnesium sulfate (2.9 g). The resulting mixture was cooled to 0° C. and freshly distilled acetaldehyde (835 μl, 14.78 mmol) was added. After 6 h of stirring at room temperature, the mixture was filtered and the solvent was evaporated under reduced pressure to give the title compound (2.16 g) as an almost colorless liquid. 1H NMR (CDCl3, 500 MHz) δ 4.60 (q, J=5.40 Hz, 1H, CHCH3), 3.01 (d, J=12 Hz, 1H, CHHNH), 2.76 (d, J=12 Hz, 1H, CHHNH), 2.55-2.31 (m, 4H, CH2N), 2.28 (s, 3H, NCH3), 1.77-1.58 (m, 4H, CH2CO), 1.36 (d, J=5.40 Hz, 3H, CH3CH) ppm; 13C NMR (CDCl3, 300 MHz) δ 87.57 (CH), 57.19 (CH2), 53.14 (C), 52.96 (CH2), 46.15 (CH3), 37.28 (CH2), 35.73 (CH2), 20.32 (CH3) ppm.

후처리

  1. filtrationthe mixture was filtered
  2. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-a667713d7ea740cc8466bb9ded0c2186
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034891B2

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