1,6-Dioxaspiro[2.5]octane → tert-butyl({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)carbamate

HRID 639535Notes

Reaction equation

[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[O:16]1[C:18]2([CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH2:17]1>CO>[OH:16][C:18]1([CH2:17][N:12]2[CH2:11][CH2:10][CH:9]([CH2:8][NH:7][C:6](=[O:15])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:14][CH2:13]2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of tert-butyl(piperidin-4-ylmethyl)carbamate (22.3 g, 104 mmol) in methanol (120 mL) was added 1,6-dioxaspiro[2.5]octane (14.2 g, 124 mmol, prepared according to Satyamurthy, Nagichettiar et al., Phosphorus Sulfur, 1984, 19, 113) at room temperature. Then, the mixture was heated at 60° C. for 4 h. The volatile components were removed by evaporation and the resulting viscous oil was precipitated with a mixture of hexane and diethyl ether. The precipitate was collected by filtration and recrystallized from a mixture of n-hexane and 2-propanol to give the title compound 14.2 g (42%) as a colorless powder.

Workup

customThe volatile components were removed by evaporation
customthe resulting viscous oil was precipitated with a mixture of hexane and diethyl ether
filtrationThe precipitate was collected by filtration
customrecrystallized from a mixture of n-hexane and 2-propanol

Sources & evidence

ORD record: ord-475eeaf6878445d299d15b87f06718da
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691881B2

Reaction notes

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