Sodium Carbonate → tert-Butyl 4-[2-(trifluoromethyl)phenyl]-1,2,5,6-tetrahydropyridinecarboxylate

HRID 489668노트

반응식

HRID 489668 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.FC(F)(F)S(O[C:20]1[CH2:25][CH2:24][NH:23][CH:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=1)(=O)=O.C(OC(N1CCC(=O)CC1)=O)(C)(C)C.[Li+].CC([N-]C(C)C)C.C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O.COCCOC.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>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:20]1[CH2:25][CH2:24][NH:23][CH:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=1

참가 물질

10

반응물 6

HCID 10340Sodium CarbonateHCID 142176Phenyl triflimideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 22266210Tert-butyl 4-[(trifluoromethyl)sulfonyloxy]-1,2,5,6-tetrahydropyridinecarboxylate

생성물 1

HCID 22266248tert-Butyl 4-[2-(trifluoromethyl)phenyl]-1,2,5,6-tetrahydropyridinecarboxylate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

The title compound was prepared according to the procedure described in Preparation A using 2-(trifluoromethyl)phenylboronic acid (Aldrich) (1.89 g, 10 mmol), tert-butyl 4-[(trifluoromethyl)sulfonyloxy]-1,2,5,6-tetrahydropyridinecarboxylate [prepared by the method of Wustrow, D. J. and Wise, L. D., Synthesis, 1991, 993-995, from tert-butyl-4-oxopiperidine-1-carboxylate (Aldrich), LDA (Aldrich) and N-phenyltrifluoromethanesulfonimide (Aldrich)] (3.64 g, 11 mmol), tetrakis(triphenylphosphine)palladium (0) (Strem Chemicals) (0.578 g, 0.5 mmol), LiCi (Aldrich) (1.27g, 30 mmol), and Na2CO3 (Aldrich) (2.46 g, 30 mmol) in water (15 mL) and DME (20 mL). Purification by silica gel chromatography (5:1 hexane:EtOAc) provided the title compound as a white foam (2.01 g). MS (ESI, pos. ion) m/z: 328 (M+1); MS (ESI, neg. ion) m/z: 326 (M−1). Calc'd for C17H20F3NO2: 327.34.

후처리

  1. customThe title compound was prepared
  2. customprepared by the method of Wustrow, D
  3. custom, Synthesis, 1991, 993-995
  4. customPurification by silica gel chromatography (5:1 hexane:EtOAc)

출처 및 근거

ORD 기록
ord-62611c2b2fca4456a21b3f65b831c302
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977264B2

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