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Ammonium formate → ((2S,3R,4S)-4-Amino-4-(2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol

HRID 68372
ノート
印刷プレビュー

反応式

HRID 68372 の反応式
[NH2:1][C@@:2]1([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[C:32](Cl)[C:31]=2[F:38])[CH2:6][O:5][C@H:4]([CH2:7][O:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:3]1[CH2:28][OH:29].C([O-])=O.[NH4+]>[Pd].CO>[NH2:1][C@@:2]1([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[F:38])[CH2:6][O:5][C@H:4]([CH2:7][O:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:3]1[CH2:28][OH:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 86707811((2S,3R,4S)-4-Amino-4-(3-chloro-2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol

生成物 1

HCID 86707812((2S,3R,4S)-4-Amino-4-(2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol収率 99.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887
Methanol
溶媒

実験手順

A mixture of ((2S,3R,4S)-4-amino-4-(3-chloro-2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol (4.49 g, 8.4 mmol), ammonium formate (3.2 g, 50 mmol) and 10% palladium on carbon (500 mg) in dry MeOH (40 mL) was stirred at RT under nitrogen overnight. The catalyst was removed by filtration through Celite®—washing with methanol. The filtrate was evaporated and the residue was partitioned between DCM (100 mL) and saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous layer was further extracted with DCM (100 mL×4). The combined extracts were dried (Na2SO4), filtered and evaporated to give the title compound (4.18 g). 1H NMR (400 MHz, MeOH-d4) δ ppm: 2.73-2.84 (m, 1 H) 3.17 (dd, J=10.03, 5.14 Hz, 1 H) 3.27 (dd, J=9.96, 3.61 Hz, 1 H) 3.65-3.79 (m, 2 H) 3.88 (dd, J=8.93, 3.06 Hz, 1 H) 4.16-4.24 (m, 1 H) 4.27 (d, J=9.05 Hz, 1 H) 6.88-7.00 (m, 2 H) 7.18-7.31 (m, 9 H) 7.38-7.45 (m, 6 H) 7.58-7.67 (m, 1 H).

後処理

  1. customThe catalyst was removed by filtration through Celite®—washing with methanol
  2. customThe filtrate was evaporated
  3. customthe residue was partitioned between DCM (100 mL) and saturated aqueous NaHCO3 (50 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was further extracted with DCM (100 mL×4)
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-86562488654041a6b254a048b24267f5
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822455B2

反応ノート

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