Nitrogen → HCID 131734058、化合物

HRID 714216ノート

反応式

HRID 714216 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][CH:9]1[F:21])C.CC(C[AlH]CC(C)C)C.[OH-].[Na+]>C1COCC1.C1(C)C=CC=CC=1.O>[F:21][C@H:9]1[C@@H:8]([CH2:7][CH2:6][OH:5])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1

参加物

8

反応物 4

HCID 947NitrogenHCID 14487Diisobutylaluminum hydride2 回HCID 14798Sodium HydroxideHCID 23512083HCID 23512083、化合物

生成物 1

HCID 131734058HCID 131734058、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒2 回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 an ice-cold solution of tert-butyl 4-(2-ethoxy-2-oxoethyl)-3-fluoropiperidine-1-carboxylate (348 mg, 1.20 mmol) in dry THF (9 mL) was added DIBAL-H (2.41 mL of a 1M solution in toluene, 2.41 mmol). The reaction mixture was stirred at rt for 2 h. DIBAL-H (0.60 mL of a 1M solution in toluene, 0.60 mmol) was added again and the reaction mixture further stirred at rt for 1 h before being cooled to 0° C. Water (0.15 mL) was added followed by aq. 2N NaOH (0.30 mL). The mixture was stirred for 20 min, filtered through celite, washed with EA and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 7:3→1:1) to give the title compound as a colorless oil. LC-MS-conditions 08: tR=0.69 min; [M-CH3+H]+=233.35.

後処理

  1. stirringthe reaction mixture further stirred at rt for 1 h
  2. temperaturebefore being cooled to 0° C
  3. stirringThe mixture was stirred for 20 min
  4. filtrationfiltered through celite
  5. washwashed with EA
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by FC (hept-EA, 7:3→1:1)

出典と根拠

ORDレコード
ord-d46c42f8ac4046ecafccb067924b77c1
出典データセット
uspto-grants-2015_11
特許番号
US09187435B2

反応ノート

読み込み中…