Isobutylene oxide → 6-Hydroxy-2-{4-[(S)-7-(2-hydroxy-2-methyl-propyl)-2,7-diaza-spiro[4.4]non-2-yl]-phenyl}-3,4-dihydro-2H-isoquinolin-1-one

HRID 69435

Reaktionsgleichung

Reaktionsgleichung von HRID 69435
[CH2:1]1[C@@:5]2([CH2:9][CH2:8][NH:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([OH:26])[CH:22]=3)[C:17]2=[O:27])=[CH:12][CH:11]=1.[CH3:28][C:29]1([O:32][CH2:31]1)[CH3:30].[Br-].[Li+].CN1C(=O)CCC1>O.C(OCC)(=O)C>[OH:26][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:27])[N:16]([C:13]1[CH:14]=[CH:15][C:10]([N:2]3[CH2:3][CH2:4][C@:5]4([CH2:9][CH2:8][N:7]([CH2:28][C:29]([OH:32])([CH3:31])[CH3:30])[CH2:6]4)[CH2:1]3)=[CH:11][CH:12]=1)[CH2:25][CH2:24]2

Komponenten

7

Edukt 4

HCID 11208Isobutylene oxideHCID 13387N-methyl-2-pyrrolidoneHCID 82050Lithium BromideHCID 689918082-[(S)-4-(2,7-Diaza-spiro[4.4]non-2-yl)-phenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

Produkt 1

HCID 689882846-Hydroxy-2-{4-[(S)-7-(2-hydroxy-2-methyl-propyl)-2,7-diaza-spiro[4.4]non-2-yl]-phenyl}-3,4-dihydro-2H-isoquinolin-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 2-[(S)-4-(2,7-diaza-spiro[4.4]non-2-yl)-phenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one (0.50 g), isobutylene oxide (0.10 g), lithium bromide (0.12 g) and NMP (1 mL) was heated at 65° C. for 5 hours. The cooled reaction mixture was distributed between ethyl acetate and water. The organic phase was dried over magnesium sulfate and concentrated. In this way the product was obtained with molecular weight 435.57 (C26H33N3O3); MS (ESI): 436 (M+H+).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customIn this way the product was obtained with molecular weight 435.57 (C26H33N3O3)

Quellen und Nachweise

ORD-Eintrag
ord-6387aed4dbab48d0a1e4b19c018ce08e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822495B2

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