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

HRID 515480노트

반응식

HRID 515480 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5a5ee6f888dd4327a1af36e21b66d552
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108957B2

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