Chlorotrimethylsilane → Tert-butyl 3-(benzylamino)-3-phenylpropanoate

HRID 1592293ノート

反応式

HRID 1592293 の反応式
C([Li])CCC.[CH2:6]([NH:13][Si](C)(C)C)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CO[C@H](C1C=CC=CC=1)[C@H](OC)C1C=CC=CC=1.[C:36]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])(=[O:45])[CH:37]=[CH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.Cl[Si](C)(C)C>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:6]([NH:13][CH:38]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:37][C:36]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

8

反応物 5

HCID 6397ChlorotrimethylsilaneHCID 347555Tert-butyl cinnamateHCID 519016N-BenzyltrimethylsilylamineHCID 10988459(1R,2R)-1,2-dimethoxy-1,2-diphenylethaneHCID 178418339Butyllithium

生成物 1

HCID 11483753Tert-butyl 3-(benzylamino)-3-phenylpropanoate収率 97%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒3 回HCID 6212Chloroform溶媒

実験手順

Under an argon atmosphere, n-butyllithium (0.9 mL, 1.6 M in hexane solution, 1.5 mmol) was added to a solution of N-benzyltrimethylsilylamine (0.3 mL, 1.5 mmol) in toluene (4 mL) at −78° C. over 5 min. After stirring for 0.5 hr, a solution of (1R,2R)-1,2-dimethoxy-1,2-diphenylethane (436 mg, 1.8 mmol) in toluene (2 mL) was added, and the mixture was stirred at −78° C. for 0.5 hr. Thereto was added a solution of tert-butyl cinnamate (204 mg, 1.0 mmol) and chlorotrimethylsilane (0.63 mL, 5.0 mmol) in toluene (2 mL) over 5 min. The mixture was stirred at −78° C. for 5 hr, and quenched with saturated aqueous ammonium chloride solution (1.5 mL). After adding a saturated aqueous sodium hydrogen carbonate solution (20 mL), the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate, after which it was concentrated and subjected to silica gel column chromatography (ethyl acetate/hexane=1/25) to give the title compound (302 mg, yield 97%) as a colorless oil of [α]25D+32.5 (c 1.35, CHCl3).

後処理

  1. stirringthe mixture was stirred at −78° C. for 0.5 hr
  2. stirringThe mixture was stirred at −78° C. for 5 hr
  3. customquenched with saturated aqueous ammonium chloride solution (1.5 mL)
  4. additionAfter adding a saturated aqueous sodium hydrogen carbonate solution (20 mL)
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationafter which it was concentrated

出典と根拠

ORDレコード
ord-74c45471a807477491462f41d3d46361
出典データセット
uspto-grants-2007_11
特許番号
US07291752B2

反応ノート

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