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Benzylamine → Tert.-butyl 4-benzylamino-2-methyl-benzoate

HRID 2235053
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HRID 2235053 반응식
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([CH3:15])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH2:68]([NH2:75])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:68]([NH:75][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([CH3:15])[CH:3]=1)[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1
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참가 물질

7

반응물 4

HCID 7504BenzylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 53432590tert-Butyl 4-bromo-2-methylbenzoate

생성물 1

HCID 68583793Tert.-butyl 4-benzylamino-2-methyl-benzoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate
촉매
HCID 1140Toluene용매

실험 절차

tert.-butyl 4-bromo-2-methyl-benzoate (12 g; 43.4 mmol), caesium carbonate (21.2 g, 65 mmol), palladium(II)-acetate (1 g, 4.45 mmol) and BINAP (2.37 g, 4.40 mmol) are suspended in 150 ml of toluene under a nitrogen atmosphere and stirred for 10 minutes at ambient temperature. Then benzylamine (5.7 ml, 52.1 mmol) is added dropwise and the mixture is heated to 100° C. for two days. The mixture is then cooled, filtered to remove undissolved matter and evaporated to dryness. The oily residue is purified by chromatography (silica gel, petroleum ether/ethyl acetate 98:2). White crystals are obtained.

후처리

  1. temperaturethe mixture is heated to 100° C. for two days
  2. temperatureThe mixture is then cooled
  3. filtrationfiltered
  4. customto remove undissolved matter
  5. customevaporated to dryness
  6. customThe oily residue is purified by chromatography (silica gel, petroleum ether/ethyl acetate 98:2)
  7. customWhite crystals are obtained

출처 및 근거

ORD 기록
ord-1e310f62bf6e456f851975526636ad92
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07714000B2

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