Toluene → benzyl (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

HRID 1171846

Reaktionsgleichung

Reaktionsgleichung von HRID 1171846
[C:1]1([C@H:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](=[O:20])(O)[OH:18].[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:21]([O:18][C:17]([N:8]1[CH2:9][CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@@H:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:20])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 1382087(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinolineHCID 23113504Benzylchloride carbonate

Produkt 1

HCID 67078747benzyl (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A 25.0 g portion of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline and 24.5 g of benzyl chloride carbonate were added to a mixture of 125 ml of toluene, 19.8 g of potassium carbonate and 75 ml of water and stirred at 20° C. for 4 hours, and the organic layer was washed with 75 ml of water. The thus obtained organic layer was concentrated under a reduced pressure, purified by a silica gel column chromatography and then dried to obtain 38.0 g of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester (1H-NMR (DMSO-d6, tetramethylsilane internal standard): δ 2.73-2.83 (1H, m), 2.84-2.94 (1H, m), 3.31-3.41 (1H, m), 3.86-3.96 (1H, m), 5.12 (1H, d, J=12.8 Hz), 5.18 (1H, d, J=12.8 Hz), 6.28 (1H, s), 7.10-7.38 (14H, m), mass spectrum: m/z=344 [M+H]+ (FAB)).

Aufarbeitung

  1. washthe organic layer was washed with 75 ml of water
  2. concentrationThe thus obtained organic layer was concentrated under a reduced pressure
  3. custompurified by a silica gel column chromatography
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8b943db39ead498a9237cd6a7468cd2f
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829715B2

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