Nitrogen → HCID 131734058, 화합물

HRID 714216노트

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HRID 714216 반응식
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

참가 물질

8

반응물 4

HCID 947NitrogenHCID 14487Diisobutylaluminum hydride2회HCID 14798Sodium HydroxideHCID 23512083HCID 23512083, 화합물

생성물 1

HCID 131734058HCID 131734058, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d46c42f8ac4046ecafccb067924b77c1
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187435B2

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