Acetic Acid → HCID 77174872、化合物

HRID 1696295ノート

反応式

HRID 1696295 の反応式
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7](O)(=O)[CH3:8].S([O-])([O-])(=O)=O.[Mg+2].[O:17]1[CH:22]([C:23]([OH:25])=[O:24])[CH2:21][NH:20][C:19]2[CH:26]=[CH:27][CH:28]=[CH:29][C:18]1=2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:1]1([N:20]2[CH2:21][CH:22]([C:23]([O:25][CH2:7][CH3:8])=[O:24])[O:17][C:18]3[CH:29]=[CH:28][CH:27]=[CH:26][C:19]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 38269523,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acidHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 77174872HCID 77174872、化合物

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒2 回

反応条件

温度
25 °C

実験手順

Cyclopentanone (83 L, 0.94 mmol), acetic acid (54 L, 0.94 mmol), and magnesium sulfate (113 mg, 0.94 mmol) were added to a solution of (±)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid (Example 3a, 65 mg, 0.31 mmol) in dichloroethane (1.25 mL). Sodium triacetoxyborohydride (100 mg, 0.47 mmol) was added, followed by dichloroethane (1.25 mL), and the suspension was stirred at 25° C. for 48 h. The reaction mixture was quenched with half-saturated sodium bicarbonate, and the product was extracted using 67% EtOAc/hexane (3×25 mL). The combined organic fractions were dried over sodium sulfate and concentrated. Purification of the product by flash column chromatography (10% EtOAc/hexane) afforded the title compound as an oil. MS m/z: 276 (M+1).

後処理

  1. customThe reaction mixture was quenched with half-saturated sodium bicarbonate
  2. extractionthe product was extracted
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification of the product by flash column chromatography (10% EtOAc/hexane)

出典と根拠

ORDレコード
ord-3326df04580f4a8882341067f04b2478
出典データセット
uspto-grants-2012_04
特許番号
US08163766B2

反応ノート

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