2-TERT-BUTYLPYRROLIDINE HYDROCHLORIDE synthesis

Yield:558478-78-7 49%

Reaction Conditions:

Stage #1: 5-tert-butyl-3,4-dihydro-2H-pyrrolewith sodium tetrahydroborate in methanol at 20; for 2 h;
Stage #2: with hydrogenchloride in methanol;diethyl ether; for 1 h;

Steps:

19

To a solution of5-tert-butyl-3, 4-dihydro-2H-pyrrole (prepared from 2-pyrrolidone using the method of Mundy et al, J. Org. Chem. , 39, (13) p. 1963,1974) (200mg; 1. 6mmol) inmethanol (10m1) was added sodium borohydride portionwise (121mg; 3. 2mmol) and the solution was stirred at ambient temperature for 2h. 1. OM ethereal HCI (5ml) was added portionwise, and the mixture was stirred for1hr. The white precipitate was removed by filtration and the organic phase was evaporated under reduced pressure, to afford the title compound as a white powder (128mg; 49%). MH+ 128.'H NMR(400MHz, d4-MeOH) 6 : 3.35-3. 2 (m, 3H), 2.12-1. 95 (m, 3H), 1.83-1. 72 (m, 1H), 1.04 (s, 9H).

References:

WO2005/49023,2005,A1 Location in patent:Page/Page column 43