Sodium borohydride → (Meso-3aR,5r,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 446714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446714
[O:1]=[C:2]1[CH2:16][C@@H:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@@H:4]2[CH2:3]1.[BH4-].[Na+]>C(O)C>[OH:1][CH:2]1[CH2:16][C@@H:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:8][C@@H:4]2[CH2:3]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 10998692cis-5-Oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylic acid tert-butyl ester

Produkt 1

HCID 20753133(Meso-3aR,5r,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Compound 1019 (4 g; 0.018 mole) was dissolved in 50 mL of ethanol. Sodium borohydride was added at RT portionwise. After stirring for 3 hours, the reaction was concentrated in vacuo. The resulting oil was dissolved in DCM (200 mL), washed with water, brine, (Na2SO4), and concentrated in vacuo to yield (3aR,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate as a yellow oil (Compound 1020, 3.79 g; 93% yield); 1H NMR (CDCl3): δ 4.2 (m, 1H), 3.55 (dd, 2H), 3.4 (dd, 2H), 2.7 (m, 2H), 2.2 (m, 2H), 1.6 (m, 2H), 1.5 (s, 9H).

Aufarbeitung

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionThe resulting oil was dissolved in DCM (200 mL)
  3. washwashed with water, brine, (Na2SO4),
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cdf34d82b69745e7bb8e7b385814cb35
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481524B2

Notizen zur Reaktion

Wird geladen…