Ammonium Chloride → (S)-t-Butyl 2-(4-(3,4-dimethoxyphenoxy)-3-oxobut-1-yn-1-yl)pyrrolidine-1-carboxylate

HRID 710054노트

반응식

HRID 710054 반응식
Br[C:2](Br)=[CH:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[Li]CCCC.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[O:27][CH2:28][C:29](N(OC)C)=[O:30].[NH4+].[Cl-]>C1COCC1>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[O:27][CH2:28][C:29](=[O:30])[C:2]#[C:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 14730281(S)-t-butyl 2-(2,2-dibromovinyl)pyrrolidine-1-carboxylateHCID 867067662-(3,4-Dimethoxyphenoxy)-N-methoxy-N-methylacetamideHCID 178418339Butyllithium

생성물 1

HCID 86706767(S)-t-Butyl 2-(4-(3,4-dimethoxyphenoxy)-3-oxobut-1-yn-1-yl)pyrrolidine-1-carboxylate수율 50.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a THF (120 mL) solution of (S)-t-butyl 2-(2,2-dibromovinyl)pyrrolidine-1-carboxylate (5.326 g), n-BuLi (11.6 mL, 2.64 N hexane solution) was added dropwise at −78° C. and the mixture was stirred at the same temperature for an hour; thereafter, a THF (50 mL) solution of the compound (4.00 g) obtained in Example 14-(1) was added dropwise and temperature was raised to room temperature over an hour. The reaction mixture was added to a saturated aqueous solution of NH4Cl (400 mL) and the organic layer extracted with AcOEt (400 mL×2) was dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt/hexane) to give the titled compound (2.934 g, pale yellow oil.)

후처리

  1. extractionthe organic layer extracted with AcOEt (400 mL×2)
  2. dry with materialwas dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product, which
  6. customwas further purified by neutral silica gel chromatography (AcOEt/hexane)

출처 및 근거

ORD 기록
ord-b17b7cf490264c1dbd49b17c3ac38462
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181229B2

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