Binap, (A+-)- → N-(2-(2,2,2-Trifluoroethoxy)phenyl)-4-piperidone propylene ketal

HRID 842794노트

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HRID 842794 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[CH2:14]1[O:24][C:18]2([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[O:17][CH:15]1[CH3:16].CC(C)([O-])C.[Na+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CCOCC.[Cl-].[Na+].O.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]>[CH2:14]1[O:24][C:18]2([CH2:23][CH2:22][N:21]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH2:20][CH2:19]2)[O:17][CH:15]1[CH3:16]

참가 물질

9

반응물 4

HCID 634876Binap, (A+-)-HCID 129541174-Piperidone propylene ketalHCID 226154791-Bromo-2-(2,2,2-trifluoroethoxy)benzeneHCID 23676156Sodium t-butoxide

생성물 1

HCID 57019377N-(2-(2,2,2-Trifluoroethoxy)phenyl)-4-piperidone propylene ketal

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매HCID 57417360Sodium chloride; water용매

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온도
80 °C

실험 절차

A solution of 50 (1.786 g, 7.00 mmol) and 4-piperidone propylene ketal (2.645 g, 16.82 mmol) in toluene (30 mL) was treated with sodium tert-butoxide (1.88 g, 19.56 mmol), (S)-BINAP (44 mg, 0.07 mmol), and tris(dibenzylideneacetone)dipalladium(0) (32 mg, 0.035 mmol) at room temperature. The mixture was heated in an oil bath (80° C., 3 h). The mixture was diluted with ether and brine. The aqueous layer was extracted with two additional portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 6 mm, 20% EtOAc-80% hexane) afforded the title compound (51).

후처리

  1. extractionThe aqueous layer was extracted with two additional portions of ether
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fb00847501dd46f78e336a2a664abbff
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376503B1

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