(-)-(1S,4R)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID synthesis

10synthesis methods

Product Name:(-)-(1S,4R)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID
CAS Number:151907-79-8
Molecular formula:C11H17NO4
Molecular Weight:227.26

24424-99-5 Synthesis

24424-99-5
841 suppliers
$13.50/25G

(1S,4R)-4-AMinocyclopent-2-enecarboxylic acid hydrochloride

130931-84-9
44 suppliers
$254.00/250mg

(-)-(1S,4R)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID

151907-79-8
170 suppliers
$20.00/100mg

Yield:-

Reaction Conditions:

Stage #1: (-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloridewith N-ethyl-N,N-diisopropylamine in 1,4-dioxane;water at 0; for 0.0833333 h;
Stage #2: di-tert-butyl dicarbonate in 1,4-dioxane;water at 0 - 20;

Steps:

17

To a solution of(1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one (5.0 g, 46 mmol) in water (30.5 mL) was added aqueous HCl (2 M, 23.0 mL, 46.0 mmol). After heating at about 80° C. for about 2 h, the reaction mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. The solid was dried in a vacuum oven at about 70° C. and used without further purification. To a solution of (1S,4R)-4-aminocyclopent-2-enecarboxylic acid hydrochloride (9.20 g, 45.8 mmol) in 1,4-dioxane (15 mL) and water (18.3 mL) at about 0° C. was added DIEA (32.0 mL, 183 mmol). After stirring for about 5 min, a solution of di-tert-butyl dicarbonate (11.7 mL, 50.4 mmol) in 1,4-dioxane (5 mL) was added. The reaction mixture was warmed to ambient temperature and stirred for about 18 h. Solvent was removed under reduced pressure and the crude oil was dried in a vacuum oven at about 65° C. for about 3 h. The crude product was purified by silica gel chromatography eluting with a gradient of 80-100% EtOAc/heptane to afford (1S,4R)-4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylic acid (5.2 g, 50% over 2 steps): LC/MS (Table 2, Method a) R_t=1.81 min; MS m/z: 226 (M-H)^-.

References:

US2009/312338,2009,A1 Location in patent:Page/Page column 68

168683-02-1 Synthesis