Ethyl bromoacetate → 1-Boc-4-ethoxycarbonylmethoxypiperidine

HRID 1740078Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 10.05 g of 1-t-butoxycarbonyl-4-hydroxypiperidine and 50 ml of tetrahydrofuran was stirred with 2.6 g of sodium hydride at room temperature for 30 minutes and then cooled to 0° C. A liquid mixture of 10.02 g of ethyl bromoacetate and 50 ml of tetrahydrofuran was added, and the reaction solution was stirred for 13.5 hours. After addition of saturated ammonium chloride, the reaction solution was extracted with chloroform. The extract was dried over anhydrous sodium sulfate, the insolubles were filtered off, and the solvent was removed by evaporation. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/normal hexane=1:3→1:1) to give 6.28 g of the title compound as a pale yellow liquid.

Workup

additionwas added
extractionthe reaction solution was extracted with chloroform
dry with materialThe extract was dried over anhydrous sodium sulfate
filtrationthe insolubles were filtered off
customthe solvent was removed by evaporation
customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/normal hexane=1:3→1:1)

Sources & evidence

ORD record: ord-b0adc8e8cc184428b6cbe83edfd58aaa
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05968967

Reaction notes

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