(2S,4R) Fmoc-4-amino-1-boc-pyrrolidine-2-carboxylic acid → 4-Amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

HRID 270678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270678
[C:1]([C@@:18]1(C(O)=O)[CH2:22][C@@H:21]([NH2:23])[CH2:20][N:19]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([O:3]CC1C2C(=CC=CC=2)C2C1=CC=CC=2)=[O:2]>C(#N)C.N1CCCC1>[NH2:23][CH:21]1[CH2:20][N:19]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH:18]([C:1]([OH:3])=[O:2])[CH2:22]1

Komponenten

4

Edukt 1

HCID 67068446(2S,4R) Fmoc-4-amino-1-boc-pyrrolidine-2-carboxylic acid

Produkt 1

HCID 41840634-Amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acidAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 31268PyrrolidineKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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 3 hr. Then it was concentrated and put on high vacuum to give crude 4-amino-1-boc-pyrrolidine-2-carboxylic acid. In another round-bottomed flask, a solution of Pd2dba3 (40 mg, 5% mol)and racemic-BINAP (56 mg, 10% mol) was stirred under nitrogen in degassed toluene (8 mL) at rt for 1 h. Then 1-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-1-boc-pyrrolidine-2-carboxylic acid was added and the reaction mixture was heated under reflux for 1 h. 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)

Aufarbeitung

  1. concentrationThen it was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-be4967a0cd6d4032ae2b478a220a6caa
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449479B2

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