Hydrochloric Acid → HCID 59455657、化合物

HRID 69981ノート

反応式

HRID 69981 の反応式
[Si]([O:8][C@@H:9]1[CH2:14][C@@H:13]([F:15])[CH2:12][NH:11][CH2:10]1)(C(C)(C)C)(C)C.Cl.[CH:17]([OH:20])([CH3:19])C.[CH3:21][OH:22]>>[F:15][C@@H:13]1[CH2:14][C@@H:9]([OH:8])[CH2:10][N:11]([C:21]([O:20][CH2:17][C:19]2[CH:10]=[CH:9][CH:14]=[CH:13][CH:12]=2)=[O:22])[CH2:12]1

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3776IsopropanolHCID 59455637(3R,5R)-3-(tert-butyldimethylsilyloxy)-5-fluoropiperidine

生成物 1

HCID 59455657HCID 59455657、化合物収率 94%

実験手順

To a solution of (3R,5R)-3-(tert-butyldimethylsilyloxy)-5-fluoropiperidine (1 eq) in 30 mL of methanol was added 3.8M HCl in isopropanol (4 eq). The reaction mixture was allowed to stand at room temperature for 3 hours at which point it was concentrated under reduced pressure. The resulting residue was diluted with 120 mL of EtOAc, washed with sat. aq. sodium bicarbonate, brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=2:1) to give (3R,5R)-benzyl 3-fluoro-5-hydroxypiperidine-1-carboxylate, (94%). LC/MS (m/z): 254.2 (MH+).

後処理

  1. concentrationwas concentrated under reduced pressure
  2. additionThe resulting residue was diluted with 120 mL of EtOAc
  3. washwashed with sat. aq. sodium bicarbonate, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=2:1)

出典と根拠

ORDレコード
ord-46fa03659f6446bc980bca26afd9ea51
出典データセット
uspto-grants-2014_09
特許番号
US08822497B2

反応ノート

読み込み中…