Diisopropylethylamine → tert-butyl (3R,4R,5S)-4-(tert-butyldimethylsilyloxy)-5-methyl-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate

HRID 705240노트

반응식

HRID 705240 반응식
[Si:1]([O:8][C@@H:9]1[C@@H:14]([CH3:15])[CH2:13][NH:12][CH2:11][C@H:10]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl[C:34]1[CH:39]=[CH:38][N:37]=[CH:36][C:35]=1[N+:40]([O-:42])=[O:41]>CC(O)C>[Si:1]([O:8][C@@H:9]1[C@@H:14]([CH3:15])[CH2:13][N:12]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][C:35]=2[N+:40]([O-:42])=[O:41])[CH2:11][C@H:10]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27357814-Chloro-3-nitropyridineHCID 70901078tert-Butyl N-[(3R,4R,5S)-4-[(tert-butyldimethylsilyl)oxy]-5-methylpiperidin-3-yl]carbamate

생성물 1

HCID 59226604tert-butyl (3R,4R,5S)-4-(tert-butyldimethylsilyloxy)-5-methyl-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate수율 76%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
60 °C

실험 절차

To a solution of tert-butyl (3R,4R,5S)-4-(tert-butyldimethylsilyloxy)-5-methylpiperidin-3-ylcarbamate (1.0 equiv.) in i-PrOH (0.09 M) was added DIEA (2.5 equiv.) and 4-chloro-3-nitropyridine (1.5 equiv.). The reaction mixture was stirred at 60° C. for 2 hours. The volatiles were removed under vacuo, the residue was diluted with ethyl acetate and washed with sat. NaCl. The organic phase was dried with magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel column chromatography eluting with ethyl acetate and hexanes (1:2) to give tert-butyl (3R,4R,5S)-4-(tert-butyldimethylsilyloxy)-5-methyl-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate in 76% yield. LC/MS=467.3 (M+H), Rt=1.09 min.

후처리

  1. customThe volatiles were removed under vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with sat. NaCl
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel column chromatography
  8. washeluting with ethyl acetate and hexanes (1:2)

출처 및 근거

ORD 기록
ord-0ff659525e4745fea737d468dff5a779
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173883B2

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