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Dimethylformamide → tert-Butyl [1-(4-cyanophenyl)cyclobutyl]carbamate

HRID 2362147
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HRID 2362147 반응식
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15](Cl)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][N:21](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[Zn].O>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:20]#[N:21])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 2

HCID 6228DimethylformamideHCID 57805484tert-Butyl (1-(4-chlorophenyl)cyclobutyl)carbamate

생성물 1

HCID 46856381tert-Butyl [1-(4-cyanophenyl)cyclobutyl]carbamate

시약·촉매·용매 5

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 962Water용매

실험 절차

A mixture of [1-(4-Chloro-phenyl)-cyclobutyl]-carbamic acid tert-butyl ester 1-1 (prepared according to WO2008/070016; 1.57 g, 5.6 mmol), Zn(CN)2 (395 mg, 3.37 mmol), Pd2(dba)3 (257 mg, 0.28 mmol), dppf (311 mg, 0.56 mmol), Zinc powder (219 mg, 3.37 mmol) and 20 mL of DMF was heated to 100.deg.C for 2 hrs under nitrogen atmosphere. After cooling to room temperature, the mixture was poured into water and extracted with EA for three times. The combined EA layer was washed with water, brine and concentrated to give a residue, which was purified by silica gel chromatography eluting with EA/PE (3/1) to give 1.23 g of compound 1-2. MS (ESI) m/e (M+H+): observed=273.2, calculated=273.2.

후처리

  1. temperaturewas heated to 100.deg.C for 2 hrs under nitrogen atmosphere
  2. extractionextracted with EA for three times
  3. washThe combined EA layer was washed with water, brine
  4. concentrationconcentrated
  5. customto give a residue, which
  6. customwas purified by silica gel chromatography
  7. washeluting with EA/PE (3/1)

출처 및 근거

ORD 기록
ord-310dc2dc7840431fac8f42913c8642d9
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691825B2

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