1,4-Dioxa-8-azaspiro(4.5)decane → 8-(4-Chloro-3-methoxyphenyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 1804851

반응식

HRID 1804851 반응식
CC(C)([O-])C.[Na+].[O:7]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.Br[C:18]1[CH:19]=[CH:20][C:21]([Cl:26])=[C:22]([O:24][CH3:25])[CH:23]=1>CC(O)=O.CC(P(C(C)(C)C)C1C(C2[C-]=CC=CC=2)=CC=CC=1)(C)C.[Pd].C1(C)C=CC=CC=1.CC(O)(C)C>[Cl:26][C:21]1[CH:20]=[CH:19][C:18]([N:14]2[CH2:15][CH2:16][C:11]3([O:10][CH2:9][CH2:8][O:7]3)[CH2:12][CH2:13]2)=[CH:23][C:22]=1[O:24][CH3:25]

참가 물질

6

반응물 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 27695675-Bromo-2-chloroanisoleHCID 23676156Sodium t-butoxide

생성물 1

HCID 685538928-(4-Chloro-3-methoxyphenyl)-1,4-dioxa-8-azaspiro[4.5]decane수율 70%

시약·촉매·용매 2

HCID 119822622-(2'-Di-tert-butylphosphine)biphenylpalladium(II) acetate촉매HCID 22595558Toluene tert-butyl alcohol용매

반응 조건

온도
160 °C

실험 절차

A 20-mL microwave vial was charged with sodium tert-butoxide (537 mg, 5.59 mmol), acetato(2′-di-t-butylphosphino-1,1′-biphenyl-2-yl)palladium (II) (259 mg, 0.559 mmol) and a stir bar. The vial was sealed and purged with nitrogen. A solution of 1,4-dioxa-8-azaspiro[4.5]decane (800 mg, 5.59 mmol) and 5-bromo-2-chloroanisole (1361 mg, 6.15 mmol) in 5:1 toluene/t-BuOH (12 mL) was added via syringe. The mixture was heated by microwave (300 W) at 160° C. for 10 min and then cooled and partitioned between EtOAc and brine. The aqueous phase was extracted with EtOAc and the organic phases were combined. The resultant solution was dried (Na2SO4) and concentrated on a rotary evaporator to give the crude product. The crude product was purified by flash chromatography using a 40 g silica gel cartridge column and gradient elution with EtOAc/hexanes to afford 8-(4-chloro-3-methoxyphenyl)-1,4-dioxa-8-azaspiro[4.5]decane (1.1 g, 70%) as a yellow solid.

후처리

  1. customThe vial was sealed
  2. custompurged with nitrogen
  3. temperaturecooled
  4. custompartitioned between EtOAc and brine
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialThe resultant solution was dried (Na2SO4)
  7. concentrationconcentrated on a rotary evaporator
  8. customto give the crude product
  9. customThe crude product was purified by flash chromatography
  10. washa 40 g silica gel cartridge column and gradient elution with EtOAc/hexanes

출처 및 근거

ORD 기록
ord-5d1b795c616f459f9c06192e76b379db
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354432B2

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