Water → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 2198952Notes

Reaction equation

[O:1]1C[O:4][CH2:3][C:2]21CCC1C(O1)C2.CNC[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH2:21]>>[O:1]1[C:18]2([CH2:17][CH2:16][CH:15]([OH:21])[CH2:20][CH2:19]2)[O:4][CH2:3][CH2:2]1

Participants

Reactant 3

HCID 962Water

HCID 7669N-Methylbenzylamine

HCID 20448713HCID 20448713, compound

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Procedure

Spiro[7-oxabicyclo[4.1.0]heptane-3,2'-[1,4]dioxolane] was reacted with methyl(phenylmethyl)amine in the presence of water at 90° C. to give a 92% yield of trans-7-[methyl(phenylmethyl)amino[-1,4-dioxaspiro[4.5]decan-8-ol, bp 158°-161° C. (0.005 mm Hg). This amino alcohol was reacted with methanesulfonylchloride in the presence of triethylamine in methylene chloride solution at 0° C., and the resulting sulfonate ester was reacted with pyrrolidine in the presence of water at 90° C. to give a mixture of diamines, which were debenzylated by hydrogenation using a palladium on carbon catalyst to give a mixture (approximately 1:1 by nmr) of the subtitled diamines. The yield is 74% from the starting amino alcohol.

Sources & evidence

ORD record: ord-85acc93ae3bb4989b8aa5e29cf0bd242
Source dataset: uspto-grants-1982_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04360531

Reaction notes

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