Tetrahydrofuran → t-butyl (R)-2-hydroxy-1-(4-((S)-2-methylbutoxy)phenyl)ethylcarbamate

HRID 454997

Reaktionsgleichung

Reaktionsgleichung von HRID 454997
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]([O:16][C:17]([NH:19][C@H:20]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C@@H:33]([CH3:36])[CH2:34][CH3:35])=[CH:27][CH:26]=1)[C:21](OC)=[O:22])=[O:18])([CH3:15])([CH3:14])[CH3:13].[OH-].[K+]>C(OCC)(=O)C>[OH:22][CH2:21][C@H:20]([NH:19][C:17](=[O:18])[O:16][C:12]([CH3:13])([CH3:15])[CH3:14])[C:25]1[CH:26]=[CH:27][C:28]([O:31][CH2:32][C@@H:33]([CH3:36])[CH2:34][CH3:35])=[CH:29][CH:30]=1

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67438449(2R)-Methyl 2-(tert-butoxycarbonylamino)-(4-((S)-2-methyl-butoxy)-phenyl)acetate

Produkt 1

HCID 67073736t-butyl (R)-2-hydroxy-1-(4-((S)-2-methylbutoxy)phenyl)ethylcarbamateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A room temperature suspension of lithium aluminum hydride (320 mg, 8.5 mmol) and tetrahydrofuran (50 mL) was treated slowly with a solution of (2R)-Methyl 2-(tert-butoxycarbonylamino)-(4-((S)-2-methyl-butoxy)-phenyl)acetate and tetrahydrofuran (40 mL). The resulting reaction mixture was maintained 30 min, and then treated with ethyl acetate (12 mL) and an aqueous solution of potassium hydroxide (10% wt/wt, 24 mL). The mixture was allowed to stir for 1 h, then dried with MgSO4, filtered and concentrated to afford tert-butyl (R)-2-hydroxy-1-(4-((S)-2-methylbutoxy)phenyl)ethylcarbamate (2.2 g, 88% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.22 (d, J=8.6 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 5.12 (d, J=6.3 Hz, 1H), 4.74 (br. s., 1H), 3.80-3.87 (m, 3H), 3.74 (dd, J=9.1, 6.6 Hz, 1H), 1.87 (dq, J=13.0, 6.5 Hz, 1H), 1.53-1.64 (m, 2H), 1.45 (s, 9H), 1.22-1.34 (m, 1H), 1.03 (d, J=6.6 Hz, 3H), 0.97 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 324.1 [(M+H)+, calcd for C18H30NO4 324.4].

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas maintained 30 min
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9dacf3acb885491182d6dc4036ed84d6
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497271B2

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