Ammonia → [7-(tert-Butyldimethylsilyloxy)-5,6,7,8-tetrahydronaphthalen-1-yl]thiourea

HRID 600817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600817
[C:1]([Si:5]([O:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([N:19]=[C:20]=[S:21])[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[NH3:22]>C1COCC1>[Si:5]([O:8][CH:9]1[CH2:10][C:11]2[C:12]([NH:19][C:20]([NH2:22])=[S:21])=[CH:13][CH:14]=[CH:15][C:16]=2[CH2:17][CH2:18]1)([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:7])[CH3:6]

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 75581950Tert-butyl[(8-isothiocyanato-1,2,3,4-tetrahydronaphthalen-2-yl)oxy]dimethylsilane

Produkt 1

HCID 86609617[7-(tert-Butyldimethylsilyloxy)-5,6,7,8-tetrahydronaphthalen-1-yl]thiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of the product of Example 18C (1.25 g, 3.91 mmol) in THF (50 mL) was treated with 7N methanolic NH3 (5.6 mL, 3, 9.1 mmol), and the mixture was stirred at room temperature for 6 hours. The mixture was partitioned between EtOAc and H2O, and the separated organic phase was washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. Silica gel chromatography (98:2 to 95:5 CH2Cl2:CH3OH eluant) provided the title compound as a pale yellow solid, 1.27 g (97%). 1H NMR (300 MHz, DMSO-d6) δ 9.12 (s, 1H), 6.6-7.8 (br, 2H), 6.99-7.13 (m, 3H), 4.08 (m, 1H), 2.73-2.92 (m, 4H), 1.84-1.92 (m, 1H), 1.60-1.68 (m, 1H). MS (ESI+) m/z 337 (M+H).

Aufarbeitung

  1. customThe mixture was partitioned between EtOAc and H2O
  2. washthe separated organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1bd15e1e00484703b5784b8b002eab4d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902236B2

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