Nitrogen → Aluminum hydride

HRID 1683299노트

반응식

HRID 1683299 반응식
OS(O)(=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3:11].N#N.[AlH3].[CH3:15][N:16]([CH2:18][CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]=2)[NH:22][CH:21]=1)[CH3:17].[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38]>C1COCC1.CO.CCOCC.O>[AlH3:11].[CH:37]([C:36]([NH2:16])=[O:41])=[O:38].[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[CH3:15][N:16]([CH2:18][CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]=2)[NH:22][CH:21]=1)[CH3:17]

참가 물질

13

반응물 6

HCID 947NitrogenHCID 971Oxalic AcidHCID 1118Sulfuric AcidHCID 14488Aluminum hydrideHCID 190428341-(N,N-dimethylamino)-2-(5-benzylindol-3-yl)ethaneHCID 21226445Aluminium lithium hydride

생성물 3

HCID 14488Aluminum hydrideHCID 11708045GlyoxamideHCID 190428421-(N,N-dimethylamino)-2-(5-benzylindol-3-yl)ethane oxalate

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of AlH3 was prepared by addition of c.H2SO4 (1.59 g) dropwise to a cooled (ice-bath) suspension of LiAlH4 (1.226 g) in dry THF (82 mL) over 20 min. The mixture was them left to stand under dry N2 for 1 hr to allow the solids to settle. A solution of the glyoxamide (0.59 g, 1.926 mmol) in THF (110 mL) was prepared, and in a N2 atmosphere, the AlH3 solution (55 mL) was added over 5 min. The mixture was stirred for 16 hr and then H2O was added dropwise to quench excess reagent, and the THF was evaporated in vacuo. The residue was partitioned between 1M HCl/CH2Cl12 and after re-extraction of the aqueous layer (2×; CH2Cl2), the combined organic layers were washed with 1M HCl and then saturated aqueous NaCl, dried (MgSO4) and evaporated to a solid. Chromatography (silica gel; CH2Cl2 /EtOH containing 2% concentrated aqueous NH3 ; 0-12%), gave the free base: 1-(N,N-dimethylamino)-2-(5-benzylindol-3-yl)ethane, as a gum, 0.246 g (46%). This was treated with oxalic acid (0.07 g) in MeOH (2 mL) and Et2O added until crystallisation commenced. The product: 1-(N,N-dimethylamino)-2-(5-benzylindol-3-yl)ethane oxalate, was obtained as white granular crystals, 0.191 g (27%), m.p.158°-9° C.

후처리

  1. waitleft
  2. customto quench excess reagent
  3. customthe THF was evaporated in vacuo
  4. customThe residue was partitioned between 1M HCl/CH2Cl12
  5. extractionafter re-extraction of the aqueous layer (2×; CH2Cl2)
  6. washthe combined organic layers were washed with 1M HCl
  7. dry with materialsaturated aqueous NaCl, dried (MgSO4)
  8. customevaporated to a solid
  9. customChromatography (silica gel; CH2Cl2 /EtOH containing 2% concentrated aqueous NH3 ; 0-12%), gave the free base
  10. additionadded until crystallisation

출처 및 근거

ORD 기록
ord-b4d9cb8f7e7b47d9bc405e474e435971
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05637593

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