Phenol → tert-butyl ((3R)-3-hydroxy-3-(3-((tetrahydro-2H-thiopyran-3-yl)methoxy)phenyl)propyl)carbamate

HRID 2277046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277046
C([O-])([O-])=O.[K+].[K+].C1(O)C=CC=CC=1.[OH:14][C@@H:15]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=1)[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].CC1C=CC(S(O[CH2:44][CH:45]2[CH2:50][CH2:49][CH2:48][S:47][CH2:46]2)(=O)=O)=CC=1>CN(C=O)C>[OH:14][C@@H:15]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:44][CH:45]2[CH2:50][CH2:49][CH2:48][S:47][CH2:46]2)[CH:27]=1)[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]

Komponenten

6

Edukt 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamateHCID 90405933(tetrahydro-2H-thiopyran-3-yl)methyl 4-methylbenzenesulfonate

Produkt 1

HCID 131733435tert-butyl ((3R)-3-hydroxy-3-(3-((tetrahydro-2H-thiopyran-3-yl)methoxy)phenyl)propyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

K2CO3 (0.72 g, 5.24 mmol) and phenol (7, Intermediate I) (0.3 g, 1.05 mmol) were added to a solution of (tetrahydro-2H-thiopyran-3-yl)methyl 4-methylbenzenesulfonate (0.29 g, 1.10 mmol) in DMF (10 mL). The reaction mixture was heated at 100° C. under reflux overnight and then cooled. The reaction mixture was extracted with EtOAc, organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (EtOAc:hexane 10-40% gradient) gave tert-butyl ((3R)-3-hydroxy-3-(3-((tetrahydro-2H-thiopyran-3-yl)methoxy)phenyl)propyl)carbamate as a light green solid. Yield (0.21 g, 52%); 1H NMR (400 MHz, CDCl3): δ 7.24 (t, J=8.0 Hz, 1H), 6.91 (d, J=8.0 Hz, 2H), 6.78 (d, 1H), 4.87 (bs, 1H), 4.71 (bs, 1H), 3.84-3.80 (m, 2H), 3.49 (bs, 1H), 3.21-3.13 (m, 2H), 2.82-2.77 (m, 1H), 2.62-2.47 (m, 3H), 2.18 (bs, 1H), 2.08-2.04 (m, 1H), 1.91-1.74 (m, 4H), 1.45 (s, 9H), 1.30-1.20 (m, 3H); MS: m/z 382.2 [M+H]+.

Aufarbeitung

  1. temperatureunder reflux overnight
  2. temperaturecooled
  3. extractionThe reaction mixture was extracted with EtOAc, organic layer
  4. dry with materialwas dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (EtOAc:hexane 10-40% gradient)

Quellen und Nachweise

ORD-Eintrag
ord-de8322f951dc4b978f5f94b347e43e3f
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133154B2

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