Water → Tert-butyl 4-((2-(cyanomethyl)-6-methoxyphenoxy)methyl)piperidine-1-carboxylate

HRID 253236

반응식

HRID 253236 반응식
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:10][C:11]#[N:12].CS(O[CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.[Cl-].[Na+].O.C(OCC)(=O)C>[C:11]([CH2:10][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[O:1][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH2:21][CH2:20]1)#[N:12]

참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1426432-Hydroxy-3-methoxyphenylacetonitrileHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

생성물 1

HCID 66890287Tert-butyl 4-((2-(cyanomethyl)-6-methoxyphenoxy)methyl)piperidine-1-carboxylate수율 81%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
70 °C

실험 절차

To a solution of 2-hydroxy-3-methoxyphenylacetonitrile (1 g, 6.1 mmol) in DMF (12 mL) was added 1,1-dimethylethyl 4-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate (1.8 g, 6.1 mmol) and cesium carbonate (4.0 g, 12.2 mmol). The mixture was heated to 70° C. for 3 h and then cooled to rt. Water and ethyl acetate were added followed by brine to reduce emulsification. The layers were partitioned, and the aqueous phase was extracted with ethyl acetate. The organic extracts were combined, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (70% hexanes, 30% ethyl acetate) to provide 1.77 g of 1,1-dimethylethyl 4-({[2-(cyanomethyl)-6-(methyloxy)phenyl]oxy}methyl)piperidine-1-carboxylate (4.9 mmol, 81% yield) as a yellow syrup. 1H NMR (400 MHz, CDCl3): δ7.03 (t, 1H), 6.93 (dd, 1H), 6.88 (dd, 1H), 4.14 (br m, 2H), 3.88 (br d, 2H), 3.84 (s, 3H), 3.70 (s, 2H), 2.00 (m, 1H), 1.86 (br d, 2H), 1.47 (s, 9H), 1.35-1.25 (m, 2H).

후처리

  1. temperaturecooled to rt
  2. customThe layers were partitioned
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (70% hexanes, 30% ethyl acetate)

출처 및 근거

ORD 기록
ord-13b83ae05be84708ac1b04dd2c0f93b5
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872014B2

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