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Water → trans-4-amino-1-tert-butoxycarbonyl(2S)-(tert-butyldiphenylsilyloxy)methylpyrrolidine

HRID 350514
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 350514
Br[C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:3]1.[N-:33]=[N+]=[N-].[Na+].O>CN(C=O)C.CCO.[Pd]>[NH2:33][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 962WaterHCID 33557Sodium AzideHCID 69334767cis-4-bromo-1-tert-butoxycarbonyl-(2S)-(tert-butyldiphenylsilyloxy)methylpyrrolidine

Produkt 1

HCID 69332987trans-4-amino-1-tert-butoxycarbonyl(2S)-(tert-butyldiphenylsilyloxy)methylpyrrolidineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938
Palladium
Katalysator
HCID 702EthanolLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of cis-4-bromo-1-tert-butoxycarbonyl-(2S)-(tert-butyldiphenylsilyloxy) methylpyrrolidine (480 mg, 0.93 mmol) in DMF (5 ml) was added NaN3 (241 mg, 3.70 mmol) at room temperature. The reaction mixture was stirred at 70 for 3 days. Water was added thereto, and extracted with EtOAc. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo. The crude product was used to the subsequent reaction without further purification. The solution of the crude residue in EtOH (10 ml) was hydrogenated over 10% Pd—C under an atmospheric pressure at room temperature for 4 hr. The catalyst was filtered off, and the filtrate was concentrated in vacuo to give trans-4-amino-1tert-butoxycarbonyl-(2S)-(tert-butyldiphenylsilyloxy)methylpyrrolidine (400 mg, 95%) as a colorless oil. 1H-NMR (CDCl3) δ 1.06 (s, 9H), 1.32 and 1.45 (each s, total 9H), 2.20–2.35 (m, 1H), 3.05–3.18 (m, 1H), 3.55–4.05 (m, 6H), 7.35–7.41 (m, 6H), 7.61–7.69 (m, 4H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe extract was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was used to the subsequent reaction without further purification
  6. filtrationThe catalyst was filtered off
  7. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9035888213764b3ea0846d5050d64283
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07179819B2

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