Water → 4-[4-((R)-1-phenyl-ethyl)-[1,4]oxazepan-7-yl]-benzonitrile

HRID 515480ノート

反応式

HRID 515480 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:14][CH2:13][CH2:12][N:11]([C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O.[CH3:24][N:25](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[C:17]1([C@H:15]([N:11]2[CH2:10][CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([C:24]#[N:25])=[CH:3][CH:4]=3)[O:14][CH2:13][CH2:12]2)[CH3:16])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 3

HCID 962WaterHCID 6228DimethylformamideHCID 672813307-(4-bromo-phenyl)-4-((R)-1-phenyl-ethyl)-[1,4]oxazepane

生成物 1

HCID 672813254-[4-((R)-1-phenyl-ethyl)-[1,4]oxazepan-7-yl]-benzonitrile

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 15826098Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+)触媒

反応条件

温度
120 °C

実験手順

A mixture of diastereopure 7-(4-bromo-phenyl)-4-((R)-1-phenyl-ethyl)-[1,4]oxazepane (diastereomer type A) (2.0 g, 5.6 mmol), zinc(II) cyanide (0.40 g, 3.4 mmol), tris(dibenzylideneacetane)dipalladium (0.46 g, 0.50 mmol), diphenylphosphinoferrocene (0.67 g, 1.2 mmol) and water (0.02 mL, 1.0 mmol) in dimethylformamide (10 mL) was prepared at room temperature under nitrogen atmosphere. The mixture was heated to 120° C. and stirred for 8 hours. After cooling to room temperature, the reaction was quenched by the addition of 2N ammonia aqueous solution and diluted with ethyl acetate. The organic layer was separated and dried over anhydrous sodium sulfate. Concentration of the solution followed by purification of the residue by flash column chromatography on silica gel (hexane/ethyl acetate=90/10 to 60/40 as eluants) was yield 4-[4-((R)-1-phenyl-ethyl)-[1,4]oxazepan-7-yl]-benzonitrile (diastereomer type A) (0.68 g, 2.2 mmol, 40%) as brown oil.

後処理

  1. customwas prepared at room temperature under nitrogen atmosphere
  2. temperatureAfter cooling to room temperature
  3. customthe reaction was quenched by the addition of 2N ammonia aqueous solution
  4. additiondiluted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customConcentration of the solution followed by purification of the residue by flash column chromatography on silica gel (hexane/ethyl acetate=90/10 to 60/40 as eluants)

出典と根拠

ORDレコード
ord-5a5ee6f888dd4327a1af36e21b66d552
出典データセット
uspto-grants-2015_08
特許番号
US09108957B2

反応ノート

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