(3aR,7aS)-7a-(2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole → [(3S,4R)-3-amino-3-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol

HRID 1427390ノート

反応式

HRID 1427390 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:17][O:16][CH2:15][CH2:14][C@H:13]1[CH2:12][O:11][NH:10]2>[Zn].C(O)(=O)C>[NH2:10][C@:9]1([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[C@H:13]([CH2:12][OH:11])[CH2:14][CH2:15][O:16][CH2:17]1

参加物

4

反応物 1

HCID 71268925(3aR,7aS)-7a-(2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

生成物 1

HCID 71277791[(3S,4R)-3-amino-3-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

(3aR,7aS)-7a-(2,4-Difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C10) (1.06 g, 4.39 mmol) was mixed with acetic acid (10 mL); after addition of zinc powder (3.74 g, 57.2 mmol), the reaction mixture was stirred for 18 hours. Insoluble material was removed via filtration, and the filtrate was concentrated under reduced pressure. The resulting paste was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, washed with saturated aqueous sodium chloride solution, and dried over magnesium sulfate. Filtration and removal of solvent under reduced pressure provided the product. Yield: 900 mg, 3.70 mmol, 84%. 1H NMR (400 MHz, CD3OD) δ 1.71-1.78 (m, 1H), 2.00-2.12 (m, 1H), 2.40-2.48 (m, 1H), 3.37-3.40 (m, 2H), 3.50 (d, J=11.5 Hz, 1H), 3.62 (ddd, J=12.7, 11.5, 2.7 Hz, 1H), 4.01 (dd, J=11.3, 2.0 Hz, 1H), 4.09-4.15 (m, 1H), 6.96-7.05 (m, 2H), 7.64-7.71 (m, 1H).

後処理

  1. customInsoluble material was removed via filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and removal of solvent under reduced pressure
  7. customprovided the product

出典と根拠

ORDレコード
ord-3caa89e57f35491d827a988cba85fece
出典データセット
uspto-grants-2015_01
特許番号
US08933221B2

反応ノート

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