Ethylene Oxide → 2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethan-1-ol

HRID 1764468Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH2:11]1[O:13][CH2:12]1>CO>[OH:13][CH2:12][CH2:11][N:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: -20 °C

Procedure

To 23 parts of 1,4-dioxa-8-azaspiro[4.5]decane in 300 parts by volume of methanol is added 15 parts of ethylene oxide in methanol. The mixture is stirred at -20° C. for 3 hours and allowed to warm to room temperature. The solvent is removed under reduced pressure and the residue distilled to afford N-hydroxyethyl-1,4-dioxa-8-azaspiro[4.5]-decane. The corresponding tosylate is formed by reacting 16 parts of the alcohol in 75 parts of dry pyridine with 21 parts of p-toluenesulfonylchloride. The mixture is stirred at 5° C. overnight and then poured into 300 parts by volume of ice water. The resulting solid is collected by filtration to afford the tosylate.

Workup

temperatureto warm to room temperature
customThe solvent is removed under reduced pressure
distillationthe residue distilled

Sources & evidence

ORD record: ord-7ac7601acbff45a88834bcb07c7fe7df
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04116963

Reaction notes

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