1-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1253714Notes

Reaction equation

[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH:4]([C:7](OCC)=[O:8])[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (60.0 mmol, 1.0 eq.) in dry THF (80 ml) was added dropwise to a suspension of LAH (90.0 mmol, 1.5 eq.) in THF (120 ml) at 0° C. After addition of the reagent was completed the reaction mixture was stirred at 25° C. for 1 h. The reaction mixture was quenched by very slow addition of a mixture of THF-water (9:1, 36 ml) and 10% NaOH solution (7.2 ml). The mixture was then filtered through celite and filtrate was concentrated to yield the desired product as a white solid which was used in the next step without further purification. Yield: 77%

Workup

additionAfter addition of the reagent
customThe reaction mixture was quenched by very slow addition of a mixture of THF-water (9:1, 36 ml) and 10% NaOH solution (7.2 ml)
filtrationThe mixture was then filtered through celite and filtrate
concentrationwas concentrated

Sources & evidence

ORD record: ord-76ff1cd3658640be8952254ae31e1fdf
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455475B2

Reaction notes

Loading…