1,4-Dioxane hydrochloride → HCID 68644094, compound

HRID 2373290Notes

Reaction equation

HRID 2373290 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH3:13])[CH2:10][C@@H:9]1[CH2:14][OH:15])=O)(C)(C)C.[ClH:16].O1CCOCC1>>[ClH:16].[OH:15][CH2:14][C@H:9]1[CH2:10][C@H:11]([CH3:13])[CH2:12][NH:8]1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 686441541,1-Dimethylethyl (2R,4S)-2-(hydroxymethyl)-4-methyl-1-pyrrolidinecarboxylate

Product 1

HCID 68644094HCID 68644094, compound

Procedure

(2R,4S)-4-Methylpyrrolidine-2-carboxylic acid described in J. Chem. Soc. C, pp. 514-522 (1971) is reacted with di-tert-butyl dicarbonate to give (2R,4S)-1-tert-butoxycarbonyl-4-methylpyrrolidine-2-carboxylic acid. (2R,4S)-1-tert-Butoxycarbonyl-4-methylpyrrolidine-2-carboxylic acid is reacted with methyl iodide in the presence of potassium carbonate in acetonitrile solvent to give methyl (2R,4S)-1-tert-butoxycarbonyl-4-methylpyrrolidine-2-carboxylate. Methyl (2R,4S)-1-tert-butoxycarbonyl-4-methylpyrrolidine-2-carboxylate is reduced with lithium borohydride to give (2R,4S)-1-tert-butoxycarbonyl-2-hydroxymethyl-4-methylpyrrolidine. (2R,4S)-1-tert-Butoxycarbonyl-2-hydroxymethyl-4-methylpyrrolidine is reacted with 4N hydrogen chloride-dioxane to give (2R,4S)-2-hydroxymethyl-4-methylpyrrolidine hydrochloride. (2R,4S)-2-Hydroxymethyl-4-methylpyrrolidine hydrochloride is reacted with acrylonitrile to give 3-[(2R,4S)-2-hydroxymethyl-4-methylpyrrolidin-1-yl]propionitrile. In the same manner as in Example 1b (e) and using 3-[(2R,4S)-2-hydroxymethyl-4-methylpyrrolidin-1-yl]propionitrile and N,N-diethyl-2,3-dimethylbenzamide, 3-(2-(2R,4S)-2-hydroxymethyl-4-methylpyrrolidin-1-yl]ethyl)-5-methyl-2H-isoquinolin-1-one is obtained.

Sources & evidence

ORD record
ord-b5ed01bb20a642ddb240bc5e5315c1ec
Source dataset
uspto-grants-2008_12
Patent number
US07459465B2

Reaction notes

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