Reaction #69291

Reaction equation

ether

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

diisobutylaluminum hydride

→

product

Yield 77.0%

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

Yield 77.0%

Solvents

THF

DCM

Conditions

Workup

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

Procedure

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): δ □4.90 (br s, 1H), 3.27 (s, 2H), 3.06 (d, 2H), 1.5-1.17 (m, 8H), 1.44 (s, 9H).

Source