Aniline → HCID 59593434, 화합물

HRID 1098673

반응식

HRID 1098673 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.[Si:12]([O:29][C@@H:30]1[CH2:34][CH2:33][O:32][C:31]1=[O:35])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C(C(C(O)=O)O)O.[K].[Na]>C(Cl)Cl>[Si:12]([O:29][C@H:30]([CH2:34][CH2:33][OH:32])[C:31]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:35])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

6

반응물 4

HCID 6115AnilineHCID 16682925TrimethylaluminumHCID 53797635(R)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-oneHCID 86590012HCID 86590012, 화합물

생성물 1

HCID 59593434HCID 59593434, 화합물수율 78.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of aniline (356 mg, 348 μL, 3.82 mmol) in DCM (17 mL) was added trimethylaluminum (2.0M, 2.1 mL, 4.2 mmol) dropwise and the reaction mixture was stirred at RT for 40 min. A solution of (R)-3-(tert-butyldiphenylsilyloxy)-dihydrofuran-2(3H)-one (1.00 g, 2.94 mmol) in DCM (12 mL) was added dropwise and the reaction mixture was stirred at RT for 16 hours. The reaction mixture was poured into a saturated solution of sodium potassium tartaric acid and stirred for 15 min. The layers were separated, and the aqueous layer was washed with DCM (4×). The combined organics were washed with 0.1M HCl (2×), brine, dried over Na2SO4 and evaporated to dryness. Purification by silica gel chromatography (10-30% EtOAc in hexane) afforded the (R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide (1.00 g, 78%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=434.7; tR=2.16 min.

후처리

  1. stirringthe reaction mixture was stirred at RT for 16 hours
  2. stirringstirred for 15 min
  3. customThe layers were separated
  4. washthe aqueous layer was washed with DCM (4×)
  5. washThe combined organics were washed with 0.1M HCl (2×), brine
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customPurification by silica gel chromatography (10-30% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-1bbae4d73c0c41c8a7bc126a54e61afa
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143297B2

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