Dimethylformamide → tert-butyl (2S)-2-(4-cyanophenyl)morpholine-4-carboxylate

HRID 710247노트

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HRID 710247 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[CH3:21][N:22](C)C=O>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-]#N.[Zn+2].[C-]#N>[C:21]([C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1)#[N:22]

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 58097875tert-butyl (2S)-2-(4-bromophenyl)morpholine-4-carboxylate

생성물 1

HCID 66861409tert-butyl (2S)-2-(4-cyanophenyl)morpholine-4-carboxylate수율 69%

시약·촉매·용매 2

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

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온도
85 °C

실험 절차

A mixture of (S)-tert-butyl 2-(4-bromophenyl)morpholine-4-carboxylate (400 mg, 1.17 mmol), tetrakis(triphenylphosphine)palladium(0) (405 mg, 0.35 mmol) and zinc cyanide (206 mg, 1.75 mmol) in dimethylformamide (6 ml) was degassed with argon and heated in a closed tube at 85° C. on a Büchi shaker overnight. After cooling water (30 ml) was added, and the reaction mixture was extracted with ethyl acetate (50 ml). The aqueous phase was re-extracted with ethyl acetate (50 ml). The combined organic layers were re-extracted with conc. Sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (20 g silica gel, 10% ethyl acetate in heptane) to yield a white solid (233 mg, 69%). MS (ISP): 289.1 ([M+H]+), 306.2 ([M+NH4]+).

후처리

  1. customwas degassed with argon
  2. temperatureAfter cooling water (30 ml)
  3. additionwas added
  4. extractionthe reaction mixture was extracted with ethyl acetate (50 ml)
  5. extractionThe aqueous phase was re-extracted with ethyl acetate (50 ml)
  6. extractionThe combined organic layers were re-extracted with conc. Sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by flash chromatography (20 g silica gel, 10% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-6aab78deb6fd45be876d214dd2156f5c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181230B2

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