Sodium Hydroxide → 1-((Tert-butoxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acid

HRID 1922644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922644
C[O:2][C:3]([C:5]1([CH3:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)=[O:4].[OH-].[Na+]>>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:5]([CH3:17])([C:3]([OH:4])=[O:2])[CH2:6]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

Komponenten

3

Edukt 2

HCID 14798Sodium HydroxideHCID 113340041-Tert-butyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

Produkt 1

HCID 532554551-((Tert-butoxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acidAusbeute 100 %

Versuchsvorschrift

To a solution of 3-methylpyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (370 mg, 1.52 mmol) in IMS (5 mL) was added a 1M aqueous solution of sodium hydroxide (2.0 mL, 2.0 mmol). The reaction mixture was stirred at room temperature for 2 hours, and then concentrated under reduced pressure. The residue was partitioned between EtOAc and a 0.1M aqueous solution of HCl. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated to give the desired product as a white solid (348 mg, 100%). 1H NMR (400 MHz, CHCl3-d): 6 3.85-3.75 (m, 1H); 3.52-3.41 (m, 2H); 3.27-3.15 (m, 1H); 2.39-2.30 (m, 1H); 1.83-1.74 (m, 1H); 1.51-1.40 (m, 9H); 1.38 (s, 3H).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6c0749d86cec401dac88609949e26e06
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

Notizen zur Reaktion

Wird geladen…