Triphenylphosphine → 6-[(4-Fluoro-3-methylphenoxy)methyl]-1-benzyl-2-methylazepane

HRID 467479노트

반응식

HRID 467479 반응식
[CH2:1]([N:8]1[CH:14]([CH3:15])[CH2:13][CH2:12][CH2:11][CH:10]([CH2:16][OH:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][C:20]=1[CH3:26].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>ClCCl>[F:18][C:19]1[CH:24]=[CH:23][C:22]([O:17][CH2:16][CH:10]2[CH2:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:14]([CH3:15])[CH2:13][CH2:12][CH2:11]2)=[CH:21][C:20]=1[CH3:26]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 27373944-Fluoro-3-methylphenolHCID 5363146Diisopropyl azodicarboxylateHCID 58405271HCID 58405271, 화합물

생성물 1

HCID 584052656-[(4-Fluoro-3-methylphenoxy)methyl]-1-benzyl-2-methylazepane

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
23 °C

실험 절차

A mixture of (1-benzyl-7-methylazepan-3-yl)methanol (2-5, 500 mg, 2.1 mmol, 1.0 equiv), 4-fluoro-3-methylphenol (300 mg, 2.4 mmol, 1.1 equiv), and PS-triphenyl phosphine resin (1.2 g, 2.4 mmol, 1.1 equiv) in dichloromethane (25 mL) was treated with DIAD (0.46 mL, 480 mg, 2.4 mmol, 1.1 equiv) and the resulting suspension was stirred for 16 hours at 23° C. The mixture was filtered and filtrate was concentrated. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes gradient) to yield 6-[(4-fluoro-3-methylphenoxy)methyl]-1-benzyl-2-methylazepane (2-6) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.37 (m, 5H), 6.86 (m, 1H), 6.55 (m, 2H), 3.72-1.75 (m, 20H). LRMS m/z (M+H) 342.3 found, 242.2 required.

후처리

  1. filtrationThe mixture was filtered
  2. concentrationfiltrate was concentrated
  3. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes gradient)

출처 및 근거

ORD 기록
ord-32c01b6a9d714b4991b1ec293b00f8f0
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623863B2

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