Lithium borohydride → HCID 21934548、化合物

HRID 1241441ノート

反応式

HRID 1241441 の反応式
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:14]([CH3:15])[CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]=2[N:23]=1)C.[Li+].[BH4-]>C1COCC1>[OH:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:14]([CH3:15])[CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C:10]=2[N:23]=1

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 21934521HCID 21934521、化合物

生成物 1

HCID 21934548HCID 21934548、化合物収率 74.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl 6-(2-ethoxy-2-oxoethyl)-1-methyl-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxylate (26.5 g, 79.01 mmol)) in dry THF (50 mL) at room temperature was added, LiBH4 (2.0 M in THF, 59.26 mL), and the resulting mixture was heated to reflux. After 16 hours the mixture was cooled to 0° C. and carefully quenched with water. The mixture was extracted three times with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure to get the crude product, which was chromatographed on silica gel (eluent: (1:1) hexane/ethyl acetate) to afford the desired product (17.3 g, 74%) H NMR (CDCl3) δ 1.55 (s, 9H), 2.73 (t, 2H), 2.80 (s, 3H), 3.30 (t, 2H), 3.78(t, 2H), 3.85 (t, 2H), 6.76 (d, 1H), 6.85 (d, 2H), 7.28 (s, 1H).

後処理

  1. customcarefully quenched with water
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto get the crude product, which
  7. customwas chromatographed on silica gel (eluent: (1:1) hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-3ac73ab2ddf049be9244197915da5740
出典データセット
uspto-grants-2006_10
特許番号
US07115596B2

反応ノート

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