Toluene → (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 2-methylpropan-2-yl ester

HRID 1171855

Reaktionsgleichung

Reaktionsgleichung von HRID 1171855
[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](OC([O-])=O)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:21][C:20]([O:19][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:18])([CH3:23])[CH3:22]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 1382087(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinolineHCID 22064466Tert-butyldicarbonate

Produkt 1

HCID 67079183(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 2-methylpropan-2-yl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A 10.00 g portion of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline and 10.41 g of tert-butyl dicarbonate were added to a mixture of 50 ml of toluene, 6.95 g of potassium carbonate and 30 ml of water and stirred at 20° C. overnight, and then the organic layer was washed with 30 ml of water. The thus obtained organic layer was concentrated under a reduced pressure and then dried to obtain 14.59 g of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 2-methylpropan-2-yl ester (1H-NMR (DMSO-d6, tetramethylsilane internal standard, 80° C.): δ 1.39 (9H, s), 2.72-2.91 (2H, m), 3.28-3.32 (1H, m), 3.80-3.89 (1H, m), 6.18 (1H, s), 7.07-7.33 (9H, m), mass spectrum: m/z=310 [M +H]+ (FAB)).

Aufarbeitung

  1. washthe organic layer was washed with 30 ml of water
  2. concentrationThe thus obtained organic layer was concentrated under a reduced pressure
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-597f24066c024dbba993abfd61a7a4d4
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829715B2

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