Methane → 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

HRID 458475

Reaktionsgleichung

Reaktionsgleichung von HRID 458475
[N+](=C[C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:5])=[N-].C.C[OH:20]>C([O-])(=O)C1C=CC=CC=1.[Ag+]>[C:11]([N:7]1[CH2:8][CH2:9][CH2:10][C@H:6]1[C:4]([OH:5])=[O:20])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Komponenten

5

Edukt 3

HCID 297MethaneHCID 887MethanolHCID 53788513(S)-tert-Butyl 2-(2-diazoacetyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 164649Silver benzoateKatalysator

Versuchsvorschrift

tert-Butyl (2S)-2-(diazoacetyl)-1-pyrrolidinecarboxylate (16 g, 46 mmol) was dissolved in 50 mL anhydrous methanol. Silver benzoate (0.1 mL of a 1 g solution in 12 mL TEA) was added. After 14 at room temperature, Norit was added and the mixture was concentrated in vacuo. Purifcation on SiO2 (hexanes:EtOAc 6:1 then 4:1) provided the methyl ester as a clear oil (8.35 g, 34.3 mmol, 69% from Boc-proline): 1H NMR (400 MHz, CDCl3) δ 4.12 (bs, 1H), 3.65 (s, 3H), 3.34 (m, 2H), 2.85 (m, 1H), 2.29 (dd, J=9.6, 15.2 Hz, 1H), 2.1 (m, 1H), 1.8–1.6 (m, 3H), 1.44 (s, 9H) ppm. ESMS m/z 244 (MH)+, 144 (MH−C5H8O2)+.

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-39493a3142874f9bbc04068b688530cc
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189851B2

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