Nitrogen → HCID 59382877, 화합물

HRID 2355402노트

반응식

HRID 2355402 반응식
N#N.[F:3][C:4]([F:21])([F:20])[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)=[O:6].C(=O)=O.CC(C)=O.[CH3:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][Mg]Cl.[NH4+].[Cl-]>C(OCC)C.C1COCC1>[F:21][C:4]([F:3])([F:20])[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:8]1)([OH:6])[CH2:34][CH2:33][CH2:32][CH2:31][O:30][CH3:29]

참가 물질

8

반응물 5

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 18522661Acetone cardiceHCID 49759206tert-Butyl 3-(trifluoroacetyl)piperidine-1-carboxylateHCID 178495008HCID 178495008, 화합물

생성물 1

HCID 59382877HCID 59382877, 화합물수율 15%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Under protection of N2 gas, tert-butyl 3-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate (102 mg, 0.363 mmol) was dissolved dry THF (8 mL) and cooled to −78° C. (dry ice/acetone bath). 1.22 M methoxybutylmagnesium chloride in THF (600 μL, 2 equiv) solution was added slowly. After 10 min, the reaction was allowed to warm up to rt slowly. After 2 h, satd aq NH4Cl (15 mL) solution was added to the reaction mixture. The mixture was diluted with diethyl ether and the layers were separated. The aqueous layer was extracted with diethyl ether (3×10 mL). The combined organic layers were washed with brine (10 mL) and dried over Na2SO4. After concentration, the crude product was purified by prep HPLC to afford tert-butyl 3-(1,1,1-trifluoro-2-hydroxy-6-methoxyhexan-2-yl)piperidine-1-carboxylate (20 mg, 15%).

후처리

  1. waitAfter 2 h
  2. additionwas added to the reaction mixture
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with diethyl ether (3×10 mL)
  5. washThe combined organic layers were washed with brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration
  8. customthe crude product was purified by prep HPLC

출처 및 근거

ORD 기록
ord-27ce670f38404cc38dc2dbf48b09ca42
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754737B2

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