Dimethylformamide → tert-Butyl 4-cyanophenethylcarbamate

HRID 44418노트

반응식

HRID 44418 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[CH3:18][N:19](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1)#[N:19]

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 14221818[2-(4-Bromo-phenyl)ethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 21955533tert-Butyl 4-cyanophenethylcarbamate수율 31%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

반응 조건

온도
150 °C

실험 절차

Compound 113 (530 mg, 1.8 mmol) was dissolved in dry DMF (17 mL) under N2. Zn(CN)2 (416 mg, 3.6 mmol) and Pd(PPh3)4 (200 mg, 0.18 mmol) was added. The reaction mixture was stirred and heated at 150° C. in a microwave instrument (CEM Discover®) for 20 min and the reaction mixture was then concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with EtOAc/hexanes (20˜80%) to yield 114 (540 mg, 31%) as a white solid. MS (APCI, negative): m/z 245 [M−H]+.

후처리

  1. concentrationthe reaction mixture was then concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel eluting with EtOAc/hexanes (20˜80%)

출처 및 근거

ORD 기록
ord-6655b0516066424fbb705918d32a36c6
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541423B2

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