Nitrogen → tert-Butyl 3,3-difluoro-4-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 714209ノート

反応式

HRID 714209 の反応式
N#N.C([O:5][C:6](=O)[CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]1([F:22])[F:21])C.CC(C[AlH]CC(C)C)C.[OH-].[Na+]>C1COCC1.O>[F:22][C:9]1([F:21])[CH:8]([CH2:7][CH2:6][OH:5])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:10]1

参加物

7

反応物 4

HCID 947NitrogenHCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 73977801Tert-butyl 4-(2-ethoxy-2-oxoethyl)-3,3-difluoropiperidine-1-carboxylate

生成物 1

HCID 86695049tert-Butyl 3,3-difluoro-4-(2-hydroxyethyl)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of tert-butyl 4-(2-ethoxy-2-oxoethyl)-3,3-difluoropiperidine-1-carboxylate (177 mg, 0.57 mmol) in dry THF (5.8 mL) was added DIBAL-H (1.0 M solution in THF, 1.15 mL, 1.15 mmol) at 0° C. The reaction mixture was stirred at rt for 2 h. The mixture was cooled down to 0° C., successively treated with H2O (0.23 mL) and 2N aq. NaOH (0.45 mL). The mixture was stirred at rt for 20 min, filtered through celite, washed with EA and the filtrate concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 1:1→1:2) and the title compound obtained as a colorless oil. LC-MS-conditions 08: tR=0.74 min; [M-CH3+H]+=251.34.

後処理

  1. temperatureThe mixture was cooled down to 0° C.
  2. stirringThe mixture was stirred at rt for 20 min
  3. filtrationfiltered through celite
  4. washwashed with EA
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe crude residue was purified by FC (hept-EA, 1:1→1:2)

出典と根拠

ORDレコード
ord-71299ff893e843beab2d0e6722a11f9a
出典データセット
uspto-grants-2015_11
特許番号
US09187435B2

反応ノート

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