ChemicalBook CAS DataBase List (2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID

(2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID synthesis

8synthesis methods

Product Name:(2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID
CAS Number:132622-69-6
Molecular formula:C10H18N2O4
Molecular Weight:230.26

176486-63-8 Synthesis

(2S,4R)-FMOC-4-AMINO-1-BOC-PYRROLIDINE-2-CARBOXYLIC ACID

176486-63-8
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$33.00/100mg

(2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID

132622-69-6
95 suppliers
$55.00/100mg

Yield:-

Reaction Conditions:

with pyrrolidine in acetonitrile at 20; for 3 h;

Steps:

G.III.357.1 Example 357: Preparation of Compound 357; Step 1:
To a solution of (2S, 4R)Fmoc-4-amino-1-boc-pyrrolidine-2-carboxylic acid (400 mg, 0.884 mmol) in acetonitrile (15 mL), five drops of pyrrolidine was added. The reaction mixture was stirred at rt for 3hr. Then it was concentrated and put on high vacuum togive crude 4-amino-1-boc-pyrrolidine-2-carboxylic acid. In another round-bottomed flask, a solution ofPd2dba3 (40 mg, 5% mol) and racemic-BINAP (56 mg, 10% mol) was stirred under nitrogen in degassed toluene (8mL) at rt forlh. Then1-chloroisoquinoline (216 mg, 1.326 mmol) and sodium t-butoxide (340 mg,3.536 mmol) were added and the reaction mixture was stirred for 30 min. Then 4-amino-l-boc-pyrrolidine-2-carboxylic acid was added and the reaction mixture was heated under reflux for lh. Water was added to quench the reaction and the aqueous layer was separated and filtered through filter paper. It was then concentrated and purified by Prep. HPLC to give coupled product as TFA salt. (165 mg, 40% yield) 'H NMR(CD30D, 400 MHz)8 1.44 (m, 9H), 2.51-2. 74 (m, 2H), 3.64 (m,1H), 4.01 (m,1H), 4.49 (m,1H), 4.64 (m,1H), 7.30 (d, J=6.85 Hz,1H), 7.58 (d, J=6.85 Hz,1H), 7.79 (m,1H), 7.91-7. 99 (m, 2H), 8.56 (d, J=8. 56 Hz,1H). LC-MS (retention time: 1.707 min. ), MS m/z 358(MH+).

References:

BRISTOL-MYERS SQUIBB COMPANY WO2003/99274, 2003, A1 Location in patent:Page 493-494