(S)-(-)-N-Benzyl-1-phenylethylamine → methyl 3-{R}-[benzyl-({S}-1-phenyl-ethyl)-amino]-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate

HRID 396724

Reaktionsgleichung

Reaktionsgleichung von HRID 396724
[CH2:1]([NH:8][C@@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:22]([N:29]1[C:38]2[C:33](=[CH:34][C:35]([CH:39]=[CH:40][C:41]([O:43][CH3:44])=[O:42])=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>O1CCCC1>[CH2:1]([N:8]([C@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:16])[C@@H:39]([C:35]1[CH:34]=[C:33]2[C:38](=[CH:37][CH:36]=1)[N:29]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:30][CH2:31][CH2:32]2)[CH2:40][C:41]([O:43][CH3:44])=[O:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 54398523Methyl 3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)acrylateHCID 178418339Butyllithium

Produkt 1

HCID 21354704methyl 3-{R}-[benzyl-({S}-1-phenyl-ethyl)-amino]-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A solution of (S)-N-benzyl-α-methylbenzylamine (2.6 ml) in anhydrous tetrahydrofuran (50 ml), cooled to −70° C. and under nitrogen, was treated dropwise with a solution of butyllithium in hexanes (5 ml, 2.5M) over about 5 minutes to give a red solution. After stirring at −70° C. for a further 40 minutes the mixture was treated dropwise with a solution of methyl 3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)acrylate [2.0 g, Reference Example 7(d)] in tetrahydrofuran (20 ml) over about 10 minutes. Stirring was continued at low temperature for a further 20 minutes and then the reaction mixture was allowed to warm to room temperature. The mixture was partitioned between ether and water, the layers separated, and the organic layer washed with water then with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petrol (initially 1:9 and then 15:85, v/v) to give the title compound as a viscous, colourless oil, 1.5 g.

Aufarbeitung

  1. customto give a red solution
  2. stirringStirring
  3. waitwas continued at low temperature for a further 20 minutes
  4. temperatureto warm to room temperature
  5. customThe mixture was partitioned between ether and water
  6. customthe layers separated
  7. washthe organic layer washed with water
  8. dry with materialwith brine, then dried
  9. customevaporated
  10. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petrol (initially 1:9

Quellen und Nachweise

ORD-Eintrag
ord-f504505246fc43f2b89bbd34262b5278
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608084B1

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