Reaktion #89692

Reaktionsgleichung

benzyl (1S,3S,4S)-3-acetamido-3-(tert-butylcarbamoyl)-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)cyclopentylcarbamate

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subject compound

Ausbeute 100.0%

(1S,2S,4S)-1-acetamido-4-amino-N-tert-butyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)cyclopentanecarboxamide

Ausbeute 100.0%

Lösungsmittel

ethyl acetate methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepurged with hydrogen
2. 2
   SonstigeThe mixture was purged with nitrogen
3. 3
   Filtrationcarefully filtered through a pad of Celite® (without letting filter pad dry)
4. 4
   Einengenthe filtrate concentrated in vacuo

Vorschrift

While under nitrogen, a stirred solution of benzyl (1S,3S,4S)-3-acetamido-3-(tert-butylcarbamoyl)-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)cyclopentylcarbamate (0.544 g, 1.00 mmol) in 4:1 ethyl acetate/methanol (20 mL) was treated with 20% Pd(OH)2/C (0.30 g), purged with hydrogen, and stirred under a balloon for 18 h. The mixture was purged with nitrogen and carefully filtered through a pad of Celite® (without letting filter pad dry) and the filtrate concentrated in vacuo to afford 0.409 g (100%) of the subject compound as a white solid. NMR (CDCl3): δ 6.72 (br s, 1 H), 6.67 (br s, 1 H), 3.63 (m, 1 H), 2.80 (m, 1 H), 2.57 (m, 1 H), 1.75-2.00 (m, 4 H), 1.93 (s, 3 H), 1.00-1.50 (m, 3 H), 1.25 (s, 9 H), 1.17 (s, 12 H), 0.60-0.75 (m, 2 H). MS (M+1): 410.5.

Quelle