1,3-Propanediamine → Benzyl (3-aminopropyl)carbamate

HRID 1457950Notes

Reaction equation

[CH2:1]([NH2:5])[CH2:2][CH2:3][NH2:4].CS(O)(=O)=O.[CH2:11]([O:18][C:19](Cl)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[K+]>C(COC)OC.C(O)C>[CH2:11]([O:18][C:19]([NH:4][CH2:3][CH2:2][CH2:1][NH2:5])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 20 °C

Procedure

In the process for the preparation of the novel compound of the general formula (I) according to the aforesaid second aspect of this invention, there is employed as the starting compound such a mono-amino-protected derivative of the α,ω-alkanediamine as represented by the general formula (II) shown hereinbefore. This mono-amino-protected derivative of the formula (II) may be prepared by anyone of known various methods but preferably may be prepared in accordance with the method of Atwell & Denny [see the "Synthesis", page 1032 (1984)]. More specifically, for example, an aqueous solution of propane-1,3-diamine is adjusted to pH 3.8 with methane-sulfonic acid, followed by addition of ethanol. The resulting solution is added dropwise with a solution of benzyloxycarbonyl chloride in dimethoxyethane under stirring at 20° C. At the same time, to the resulting mixture is added an aqueous solution of potassium acetate so that the pH of the reaction mixture is maintained at 3.5-4.5 during the reaction, whereby one of the amino groups of the propane-1,3-diamine can be selectively benzyloxycarbonylated to afford N-(benzyloxycarbonyl)-propane-1,3-diamine in a high yield (see Referential Example 2 given hereinafter).

Workup

custompreferably may be prepared in accordance with the method of Atwell & Denny [
customthe "Synthesis", page 1032 (1984)]

Sources & evidence

ORD record: ord-55cfef51460c413bbf5677771e3153f1
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849797

Reaction notes

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