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HCID 70558534、化合物 → HCID 70556450、化合物

HRID 707681
ノート
印刷プレビュー

反応式

HRID 707681 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:16][O:15][C@H:14]([CH2:17][O:18][C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:13]1[CH2:12][O:11][NH:10]2>C(O)(=O)C.[Zn]>[NH2:10][C@@:9]1([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH2:16][O:15][C@H:14]([CH2:17][O:18][C:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C@H:13]1[CH2:12][OH:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 70558534HCID 70558534、化合物

生成物 1

HCID 70556450HCID 70556450、化合物

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

Zinc powder (20.0 g) was added to a solution containing (3aR,4S,6aS)-6a-(2,3-difluorophenyl)-4-((trityloxy)methyl)hexahydrofuro[3,4-c]isoxazole, obtained in Preparation Example 1-(2), (15.51 g) in acetic acid (120 mL) at 0° C. The reaction solution was allowed to warm to RT and stirred for 18 h. The insoluble matter was separated by filtration through Celite®, washing with acetic acid (100 mL) and AcOEt (300 mL), and the filtrate was concentrated. Saturated aqueous NaHCO3 solution was added carefully to neutralize the residue, and the mixture was extracted with EtOAc (3×200 mL). The combined organic layers were dried over MgSO4 and evaporated to obtain the title compound (15.42 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 2.60-2.68 (m, 1H), 2.85 (br s, 3H), 3.29 (d, J=4.8 Hz, 2H), 3.66 (dd, J=12.1, 4.8 Hz, 1H), 3.89-3.99 (m, 2H), 4.31 (d, J=9.1 Hz, 1H), 4.34-4.40 (m, 1H), 7.04-7.19 (m, 2H), 7.20-7.33 (m, 10H), 7.39-7.50 (m, 6H)

後処理

  1. customat 0° C
  2. customThe insoluble matter was separated by filtration through Celite®
  3. washwashing with acetic acid (100 mL) and AcOEt (300 mL)
  4. concentrationthe filtrate was concentrated
  5. additionSaturated aqueous NaHCO3 solution was added carefully
  6. extractionthe mixture was extracted with EtOAc (3×200 mL)
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. customevaporated

出典と根拠

ORDレコード
ord-21d912a09d2a4496ba3885fe59e240a7
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09175013B2

反応ノート

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