134003-84-2

134003-84-2 - Names and Identifiers

Name	tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride
Synonyms	(1R,4R) (1R,4R)-2-Boc- 2,5-diazabicyclo[2.2.1]heptane-HCl tert-Butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride 1,1-Dimethylethyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1R,4R)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride (1R,4R)-tert-butyl 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate HCl 134003-84-2
CAS	134003-84-2

134003-84-2 - Physico-chemical Properties

Molecular Formula	C10H18N2O2
Molar Mass	198.26
Density	1.104±0.06 g/cm3(Predicted)
Boling Point	276.4±15.0 °C(Predicted)
pKa	9.74±0.20(Predicted)
Storage Condition	2-8°C

134003-84-2 - Risk and Safety

WGK Germany

134003-84-2 - Reference Information

apply

(1R,4R)-2, 5-diazabicyclo [2.2.1] heptane-2-carboxylic acid tert-butyl ester is a commonly used pharmaceutical intermediate, which can be synthesized from (1R,4R)-2-(benzyl)-2, 5-diazabicyclo [2.2.1] heptane dihydrobromate as raw material (1R,4R)-2-(benzyl)-2, 5-diazabicyclo [2.2.1] heptane dihydrobromide, then debenzyl to obtain (1R,4R)-2, 5-diazabicyclo [2.2.1] heptane-2-carboxylic acid tert-butyl ester.

preparation

step A:(4S,2R)-4-methanesulfonyloxy-2-methanesulfonyloxymethyl-pyrrolidine -1-
carboxylic acid tert-butyl ester. To 4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (10.85g,50.0mmol) in pyridine (50ml) over 20 minutes methanesulfonyl chloride (10.8mL,140mmol) was added to the solution. After stirring for 16 h, the reaction mixture was concentrated to dryness, diluted with a saturated aqueous solution of Na2CO3 and extracted with EtOAc(2x). The combined organic layers were dried (MgSO4), filtered, and concentrated to give the title compound as a slowly solidifying oil (14.4g,84%). Step B:(1R,4R)-2, 5-diazabicyclo [2.2.1] heptane-2-carboxylic acid tert-butyl ester. (4S,2R)-4-methanesulfonyloxy-2-methanesulfonyloxymethyl-pyrrolidine-L-carboxylic acid tert-butyl ester (1G, 2.7mmol) the heterogeneous mixture in ammonium hydroxide (27 wt% aqueous solution, 10ml) was warmed to 65 °c in a sealed tube for 16 hours during which time the mixture became homogeneous. The aqueous layer was extracted with CH2Cl2(2x) and the combined organic layers were dried over Na2SO4, filtered and concentrated to give (1R,4R)-2, 5-diazabicyclo [2.2.1] heptane-2-carboxylic acid tert-butyl ester as a yellow solid (66% mg,).

Last Update：2024-04-09 02:00:14