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

HRID 2235053
ノート
印刷プレビュー

反応式

HRID 2235053 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate
触媒
HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1e310f62bf6e456f851975526636ad92
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07714000B2

反応ノート

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