Water → N-Methyl-4-benzyloxy-2-fluoroaniline

HRID 388022

반응식

HRID 388022 반응식
N1([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][C:13]=2[F:26])C2C=CC=CC=2N=N1.[BH4-].[Na+].O.C(OCC)(=O)C.O1CCCC1>CN(C)C=O.CO.C(O)C>[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:14][C:13]=1[F:26]

참가 물질

8

반응물 4

HCID 962WaterHCID 4311764Sodium borohydride2회HCID 21939870Tetrahydrofuran ethyl acetateHCID 22936313N-{1-(1H-Benzotriazolyl)methyl}-4-benzyloxy-2-fluoroaniline

생성물 1

HCID 22936658N-Methyl-4-benzyloxy-2-fluoroaniline수율 64.9%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

After dissolving N-{1-(1H-benzotriazolyl)methyl}-4-benzyloxy-2-fluoroaniline (14.13 g, 40.56 mmol) in N,N-dimethylformamide (200 ml), methanol (150 ml) and ethanol (50 ml), there was added sodium borohydride (3.06 g, 81.12 mmol) and the mixture was stirred for 2.5 hours at room temperature. There was further added sodium borohydride (0.78 g, 20.28 mmol), and the mixture was stirred for 13.5 hours at room temperature. Water was added to the reaction solution, extraction was performed with ethyl acetate-tetrahydrofuran, the extract was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was adsorbed onto silica gel and purified by silica gel column chromatography (hexane-ethyl acetate system) to obtain the title compound (5.98 g, 26.31 mmol, 64.87%) as light yellow crystals.

후처리

  1. stirringthe mixture was stirred for 13.5 hours at room temperature
  2. washthe extract was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. custompurified by silica gel column chromatography (hexane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-1ce321c63ebf4659ab4778e9a44e8a33
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372981B2

연결된 노트

불러오는 중…