Ammonium Chloride → (R)-tert-butyl 3-(benzyl((S)-1-phenylethyl)amino)-3-(6-methylpyridin-3-yl)propanoate

HRID 657761

반응식

HRID 657761 반응식
[CH2:1]([NH:8][C@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH3:22][C:23]1[N:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:25][CH:24]=1.[NH4+].[Cl-]>C1COCC1>[CH2:1]([N:8]([C@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])[C@@H:29]([C:26]1[CH:27]=[N:28][C:23]([CH3:22])=[CH:24][CH:25]=1)[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 66872019(E)-tert-butyl 3-(6-methylpyridin-3-yl)acrylateHCID 178418339Butyllithium

생성물 1

HCID 66871888(R)-tert-butyl 3-(benzyl((S)-1-phenylethyl)amino)-3-(6-methylpyridin-3-yl)propanoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (S)—N-benzyl-1-phenylethanamine (3.64 g, 17.26 mmol) in THF (40 mL) at −70° C., was added dropwise n-BuLi (1.6 M, 14.7 mmol) over a period of 30 min and stirred further. After 1 h, a solution of (E)-tert-butyl 3-(6-methylpyridin-3-yl)acrylate (2.7 g, 12.3 mmol) in THF was added slowly to the above mixture and stirred further. After 2 h, sat. NH4Cl solution was added to the reaction mixture and extracted with EtOAc (3×). The combined organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo to afford a residue. Purification of the residue by column chromatography (Neutral Al2O3, Et2O/Pet ether 5:95) afforded the title compound.

후처리

  1. stirringstirred further
  2. waitAfter 2 h
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto afford a residue
  7. customPurification of the residue by column chromatography (Neutral Al2O3, Et2O/Pet ether 5:95)

출처 및 근거

ORD 기록
ord-6f1fa0f4086d4303a6d44431a267c06e
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076345B2

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