1-Phenethylamine, (-)- → (7bR,11aS)-N-[(1S)-1-phenylethyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-amine

HRID 47585

Reaktionsgleichung

Reaktionsgleichung von HRID 47585
[CH3:1][C@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:11]1[CH:12]=[C:13]2[C:17]3=[C:18]([CH2:20][S:21][CH2:22][CH2:23][N:16]3[C@H:15]3[CH2:24][CH2:25][N:26](C(OC(C)(C)C)=O)[CH2:27][C@@H:14]23)[CH:19]=1>>[C:3]1([C@@H:2]([NH:9][C:11]2[CH:12]=[C:13]3[C:17]4=[C:18]([CH2:20][S:21][CH2:22][CH2:23][N:16]4[C@H:15]4[CH2:24][CH2:25][NH:26][CH2:27][C@@H:14]34)[CH:19]=2)[CH3:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

3

Edukt 2

HCID 758181-Phenethylamine, (-)-HCID 86586435tert-butyl (7bR,11aS)-6-bromo-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate

Produkt 1

HCID 60071869(7bR,11aS)-N-[(1S)-1-phenylethyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-amine

Versuchsvorschrift

Using (S)-(−)-α-methylbenzylamine and following the procedures described in EXAMPLE 168, tert-butyl (7bR,11aS)-6-bromo-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate from EXAMPLE 7, Part A was converted into the title compound of EXAMPLE 169. 1H NMR(CDCl3) δ 7.40-7.20 (m, 5H), 6.22 (d, 1H, J=2.2 Hz), 6.14 (d, 1H, J=2.2 Hz), 4.39 (q, 1H, J=6.6 Hz), 3.62 (ABq, 2H, JAB=15.5 Hz), 3.55-3.43 (m, 1H), 3.32-3.20 (m, 2H), 3.05-2.81 (m, 4H), 2.77-2.60 (m, 1H), 2.50 (dd, 1H, J=12.8, 9.7 Hz), 2.00-1.85 (m, 2H), 1.49 (d, 3H, J=6.6 Hz). LRMS (ES)+: 366.4 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-2cdc109eb4404ad59ad9f6d1b4dbeb9a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699852B2

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