Triethylamine → Benzyl [(3S)-1-(3-bromo-5-nitropyridin-4-yl)piperidin-3-yl]carbamate

HRID 924437ノート

反応式

HRID 924437 の反応式
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1Cl.[NH:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13]1.C(N(CC)CC)C>C(O)(C)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13]1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 1514175Benzyl (3S)-piperidin-3-ylcarbamateHCID 125100523-Bromo-4-chloro-5-nitropyridine

生成物 1

HCID 86726888Benzyl [(3S)-1-(3-bromo-5-nitropyridin-4-yl)piperidin-3-yl]carbamate収率 91.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3-bromo-4-chloro-5-nitropyridine (from Ark Pharm, 0.050 g, 0.21 mmol), benzyl (3S)-piperidin-3-ylcarbamate (0.059 g, 0.25 mmol), and triethylamine (0.088 mL, 0.63 mmol) in isopropyl alcohol (0.8 mL) was heated at 90° C. in a sealed vial for 16 h. The reaction mixture was diluted with EtOAc (40 mL) and water (3 mL). The layers were separated and the organic layer was washed with water (3×3 mL) and the combined aqueous phases were extracted with EtOAc (3 mL). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the sub-title compound (0.084 g). The crude product was used without further purification in the subsequent reaction. LCMS (ESI) calc. for C18H20BrN4O4[M+H]+: m/z=435.1. found 435.0/437.0.

後処理

  1. customThe layers were separated
  2. washthe organic layer was washed with water (3×3 mL)
  3. extractionthe combined aqueous phases were extracted with EtOAc (3 mL)
  4. washThe combined organic layers were washed with brine (3 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-99ea7291633e465eb1d7b9e2ad710623
出典データセット
uspto-grants-2016_03
特許番号
US09278950B2

反応ノート

読み込み中…