Lithium borohydride → HCID 21934548, 화합물

HRID 1241441노트

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HRID 1241441 반응식
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

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 21934521HCID 21934521, 화합물

생성물 1

HCID 21934548HCID 21934548, 화합물수율 74.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3ac73ab2ddf049be9244197915da5740
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115596B2

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