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Tricyclo(3.3.1.13,7)dec-1-ylmethylamine → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-((1-adamantylmethyl)amino)propan-2-ylcarbamate

HRID 75157
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 75157
[C:1]12([CH2:11][NH2:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Si:13]([O:20][CH2:21][CH:22]1[CH2:24][N:23]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>C(Cl)Cl>[Si:13]([O:20][CH2:21][C@@H:22]([NH:23][C:25](=[O:26])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:24][NH:12][CH2:11][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2)([C:16]([CH3:19])([CH3:17])[CH3:18])([CH3:15])[CH3:14]
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Komponenten

4

Edukt 2

HCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 72525716(S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate

Produkt 1

HCID 59437175(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-((1-adamantylmethyl)amino)propan-2-ylcarbamateAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (1-adamantylmethyl)amine (15 g, 52 mmol) in anhydrous CH2Cl2 (50 mL) was added tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)aziridine-1-carboxylate (13 g, 78.3 mmol). The mixture was stirred for 10 min, the solvent was removed in vacuo and the residue was stirred at 40° C. for 5 h. The mixture was diluted with EtOAc (500 mL) and washed with water (100 mL),1N aq HCl (50 mL), satd aq NaHCO3 (50 ml) and brine (50 mL), and dried over MgSO4. The solution was concentrated to give a residue, which was purified by chromatography on silica gel to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-((1-adamantylmethyl)amino)propan-2-ylcarbamate (10 g, 24%). 1H NMR: (CDCl3, 400 MHz): δ=0.041 (s, 6H), 0.882 (s, 9H), 1.44 (s, 9H), 1.49 (s, 6H), 1.65 (m, 6H), 1.94 (s, 3H), 2.23 (s, 2H), 2.62-2.81 (m, 2H), 3.67 (m, 3H), 5.30 (s, 1H).

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. stirringthe residue was stirred at 40° C. for 5 h
  3. additionThe mixture was diluted with EtOAc (500 mL)
  4. washwashed with water (100 mL),1N aq HCl (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationThe solution was concentrated
  7. customto give a residue, which
  8. customwas purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b12f6b0d30474bdbb69a09795a73ce18
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08835426B2

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