tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylate → tert-Butyl (3S,9aR)-3-[(3R)-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl]hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

HRID 1501950

Reaktionsgleichung

Reaktionsgleichung von HRID 1501950
[CH3:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C@H:12]3[O:17][CH2:16][C@@H:15]4[CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21][N:14]4[CH2:13]3)[CH:9]=2)[C:4](=[O:29])[O:3]1.C[C@@H]1CC2C(=CC=C([C@@H]3OC[C@@H]4CN(C(OC(C)(C)C)=O)CCN4C3)C=2)C(=O)O1.BrC1C=C2C(=CC=1)C(=O)O[C@H](C)C2.OC[C@@H]1NCCN(C(OC(C)(C)C)=O)C1>>[CH3:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C@@H:12]3[O:17][CH2:16][C@H:15]4[CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21][N:14]4[CH2:13]3)[CH:9]=2)[C:4](=[O:29])[O:3]1

Komponenten

5

Edukt 4

HCID 24820286tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 71270763(3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-oneHCID 71273516tert-Butyl (3R,9aS)-3-[(3R)-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl]hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylateHCID 71273517tert-Butyl (3S,9aS)-3-[(3R)-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl]hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Produkt 1

HCID 86727033tert-Butyl (3S,9aR)-3-[(3R)-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl]hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Versuchsvorschrift

8G and 8H were prepared in a similar manner as 8A and 8B except (3R)-6-Bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one and tert-butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylate were used as the starting materials. The cis/trans mixture was purified via chiral HPLC (20% 2:1 MeOH:MeCN/CO2) on OJ column. The slower eluting diastereomer was the trans isomer: 8G LC-MS: (M+1)+403; 8H: LC-MS: (M+1)+403.

Aufarbeitung

  1. customThe cis/trans mixture was purified via chiral HPLC (20% 2:1 MeOH:MeCN/CO2) on OJ column
  2. washThe slower eluting diastereomer

Quellen und Nachweise

ORD-Eintrag
ord-ba51efd342f44bde8f6b143c49164156
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206199B2

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