Reaktion #73323

Reaktionsgleichung

ether

methyl 1-[(tert-butoxycarbonyl)amino]methylcyclopentanecarboxylate

diisobutylaluminum hydride

→

product

Ausbeute 77.0%

tert-Butyl [1-(hydroxymethyl)cyclopentyl]methylcarbamate

Ausbeute 77.0%

Lösungsmittel

THF

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThis mixture was stirred for 30 minutes at ambient temperature
2. 2
   Sonstigethe organic layer was separated
3. 3
   Waschenwashed with water, and brine
4. 4
   TrocknenThe organic layer was then dried over sodium sulfate
5. 5
   Sonstigethe solvent was removed in vacuo

Vorschrift

To a solution of methyl 1-[(tert-butoxycarbonyl)amino]methylcyclopentanecarboxylate (1.50 g, 5.83 mmol) in THF (25.0 mL) at −78° C. was added dropwise 1.0 M diisobutylaluminum hydride in DCM (17.5 mL). The reaction was stirred for 2 hours with slow warming to −10° C. A saturated solution of K/Na tartrate was added, followed by ether. This mixture was stirred for 30 minutes at ambient temperature and the organic layer was separated and washed with water, and brine. The organic layer was then dried over sodium sulfate, and the solvent was removed in vacuo to afford the product (1.03 g, 77%). 1H NMR (300 MHz, CDCl3): 4.90 (br s, 1H), 3.27 (s, 2H), 3.06 (d, 2H), 1.5-1.17 (m, 8H), 1.44 (s, 9H).

Quelle