Diisobutylaluminum hydride → Ethyl 4-(hydroxymethyl)piperidine-1-carboxylate

Temperature

-78 °C

The above ester (12.8 g, 59.5 mmol, 1.0 equiv) was dissolved in 50 mL of dry CH2Cl2 under Ar and cooled to −78° C. A 1 Molar solution of DIBAL-H in CH2Cl2 (149 mL, 149 mmol, 2.5 equiv) was added dropwise over a 30 min period. The cold bath was removed and the reaction solution allowed to warm to ambient temperature. At this time EtOAc (10 mL) was added dropwise to quench the excess DIBAL-H. 100 mL of 1H HCl (aq) was added dropwise over a 30 min period with rapid stirring. The resulting mixture was filtered on a pad of diatomaceous earth and the filtrate was dried over Na2SO4, decanted and concentrated to yield 4-hydroxymethyl-piperidine-1-carboxylic acid ethyl ester as a nearly colorless oil that was used without further purification.

1. customThe cold bath was removed
2. temperatureto warm to ambient temperature
3. additionAt this time EtOAc (10 mL) was added dropwise
4. customto quench the excess DIBAL-H
5. addition100 mL of 1H HCl (aq) was added dropwise over a 30 min period with rapid stirring
6. filtrationThe resulting mixture was filtered on a pad of diatomaceous earth
7. dry with materialthe filtrate was dried over Na2SO4
8. customdecanted
9. concentrationconcentrated

ORD record

ord-e35f36f07016443db1cd096e6f5f1fcd

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06936606B2