tert-Butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamate → tert-Butyl N-allyl-N-phenacyl-carbamate

HRID 338077노트

반응식

HRID 338077 반응식
[CH2:1]([N:4]([CH2:12][C:13](N(OC)C)=[O:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].[C:19]1([Mg]Br)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[CH2:1]([N:4]([CH2:12][C:13]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:14])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH:2]=[CH2:3]

참가 물질

4

반응물 2

HCID 86697892tert-Butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamateHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 86697893tert-Butyl N-allyl-N-phenacyl-carbamate수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamate (4.0 g, 15.5 mmol) in THF (54 mL) cooled to −20° C. is added drop wise phenyl magnesium bromide (10.3 ml, 3 M in diethyl ether). The reaction is monitored by TLC, carefully quenched with saturated ammonium chloride in water (20 mL), diluted with water (100 mL) and extracted with dichloromethane. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (5:1) to give the title compound (3.2 g, 75%). 1H NMR (CDCl3) Mixture of two rotamers (51:49) δ 1.47, 1.35 (s, 9H), 3.91, 3.99 (d, 2H), 4.52, 4.65 (s, 2H), 5.07-5.16 (m, 2H), 5.72-5.87 (m, 1H), 7.41-7.50 (m, 2H), 7.52-7.60 (m, 1H), 7.88-7.95 (m, 2H).

후처리

  1. customcarefully quenched with saturated ammonium chloride in water (20 mL)
  2. additiondiluted with water (100 mL)
  3. extractionextracted with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue
  8. customThe residue is purified by silica gel flash chromatography
  9. washeluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (5:1)

출처 및 근거

ORD 기록
ord-4e3c9166c09d4342a48b04378fd7eefb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889856B2

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