Water → 4-(2-Hydroxymethylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester

HRID 41631Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:18]=[CH:17][O:16][C:15]=2[C:19](OC)=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:18]=[CH:17][O:16][C:15]=2[CH2:19][OH:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-(2-methoxycarbonylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester (2.0 g, 6.5 mmol, 1.0 eq.) in THF (60 mL) was added to a solution of LiAlH4 (490 mg, 13 mmol, 2.0 eq.) in THF (100 mL) at −30° C. The resulting solution was stirred for 1 hour and allowed to warm to 0° C., then stirred for 1 hour at 0° C. Water (0.5 mL) was added dropwise to quench the reaction. The mixture was allowed to warm to room temperature, and 15% NaOH (0.5 mL) and water (1.5 mL) was added. The solids were filtered and the filter cake was washed with EtOAc (50 mL). The filtrate was concentrated and the residue was applied onto a silica gel column and purified by chromatography with PE/EtOAc (10:1˜5:1), then by preparative HPLC to yield 4-(2-hydroxymethylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester (1.1 g) as a yellow oil.

Workup

stirringstirred for 1 hour at 0° C
customto quench
customthe reaction
temperatureto warm to room temperature
filtrationThe solids were filtered
washthe filter cake was washed with EtOAc (50 mL)
concentrationThe filtrate was concentrated
custompurified by chromatography with PE/EtOAc (10:1˜5:1)

Sources & evidence

ORD record: ord-6ae1e7844d9a4115a337282f9d9b5e41
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530663B2

Reaction notes

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