Triethylamine → 1-(4,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carbonyl)pyrrolidine

HRID 367304노트

반응식

HRID 367304 반응식
[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH3:17])([C:14](O)=[O:15])[O:13][C:9]=2[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[O:22][Si:23]([CH3:26])([CH3:25])[CH3:24])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([N:29](CC)[CH2:30][CH3:31])[CH3:28].N1CCCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>ClCCl>[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH3:17])([C:14]([N:29]3[CH2:30][CH2:31][CH2:28][CH2:27]3)=[O:15])[O:13][C:9]=2[CH:8]=[C:7]([C:18]([CH3:20])([CH3:19])[CH3:21])[C:6]=1[O:22][Si:23]([CH3:25])([CH3:26])[CH3:24])([CH3:3])([CH3:4])[CH3:2]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 232880354,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid

생성물 1

HCID 232880321-(4,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carbonyl)pyrrolidine수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In 3 ml of dichloromethane were dissolved 0.20 g of 4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid, 0.20 ml of triethylamine and 0.06 ml of pyrrolidine at room temperature, and 0.35 g of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate was added and the mixture was stirred for 4 hours. The mixture was extracted with water and diethyl ether, and the combined organic layers were washed with saturated brine and dried over anhydrous magnesium sulfate. After concentration, the residue was purified by silica gel column chromatography eluting with n-hexane containing 33% ethyl acetate to give 0.21 g of 1-(4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carbonyl)pyrrolidine as a colorless solid (yield 92%).

후처리

  1. extractionThe mixture was extracted with water and diethyl ether
  2. washthe combined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationAfter concentration
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with n-hexane containing 33% ethyl acetate

출처 및 근거

ORD 기록
ord-d3602439b0db4917a2a1a62a6a21f456
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133279

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