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

HRID 270678ノート

反応式

HRID 270678 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 31268Pyrrolidine触媒HCID 6342Acetonitrile溶媒

実験手順

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)

後処理

  1. concentrationThen it was concentrated

出典と根拠

ORDレコード
ord-be4967a0cd6d4032ae2b478a220a6caa
出典データセット
uspto-grants-2008_11
特許番号
US07449479B2

反応ノート

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