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

HRID 2362147
ノート
印刷プレビュー

反応式

HRID 2362147 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 23994Zinc触媒
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-310dc2dc7840431fac8f42913c8642d9
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691825B2

反応ノート

読み込み中…

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