Reaktion #953459

Reaktionsgleichung

alcohol

N-benzyl-3-hydroxymethylpyrrolidine

barium hydroxide hydrate

→

N-benzyl-3-pyrrolidinecarboxylic acid

Lösungsmittel

sulfuric acid

sulfuric acid

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solid was filtered
2. 2
   Waschenwashed with water
3. 3
   ExtraktionThe aqueous solution was extracted with ether
4. 4
   SonstigeCarbon dioxide was bubbled through the solution until the pH was 7.0
5. 5
   FiltrationThe solution was filtered
6. 6
   Einengenconcentrated

Vorschrift

A suspension of lithium aluminum hydride (7.50 g) in 150 ml THF was cooled to -5° C. A solution of methyl 1-benzyl-5-oxo-3-pyrrolidine carboxylate (0.064 moles, 15.0 g) in THF was added dropwise. The mixture was heated to 40° C. for 16 hours. Water (25 ml) was added. The mixture was filtered and extracted with ether. The organic phase was washed with water, dried over sodium sulfate and concentrated to yield 11.65 g of N-benzyl-3-hydroxymethylpyrrolidine. (MS) The alcohol (0.06 moles, 11.5 g) in 75 ml 2N sulfuric acid was added dropwise to a stirred solution of chromium dioxide (0.15 moles, 15.0 g) in 100 ml 2N sulfuric acid. The solution was stirred at room temperature for 16 hours. The solution was treated with barium hydroxide hydrate (0.317 mmoles, 100 g) in 250 ml hot water. The solid was filtered and washed with water. The aqueous solution was extracted with ether. Carbon dioxide was bubbled through the solution until the pH was 7.0. The solution was filtered and concentrated to yield 4.5 g of N-benzyl-3-pyrrolidinecarboxylic acid. (MS) The oil was dissolved in 50 ml methanol. Dry HC1 gas was bubbled through the solution. The solution was heated to near reflux for 4 hours and concentrated. The residue was neutralized with aqueous sodium bicarbonate. The product was extracted with ether, dried and concentrated to yield 3.0 g of methyl N-benzyl-3-pyrrolidinecarboxylate.

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