Facile synthesis of (R)-1-(1H-indol-3-yl)propan-2-amines hydrochloride from Ketones

被引：0

作者：

Peng, Zhi Guang ^{[1
,2
]}

Yao, Yuan Xiang ^{[2
]}

Yin, Dong Hong ^{[2
]}

Lu, Jian Fu ^{[2
]}

Yu, Jin Gang ^{[1
]}

Huang, Du Shu ^{[3
]}

机构：

[1] Cent South Univ Technol, Minist Educ, Key Lab Resources Chem Nonferrous Met, Changsha 410083, Hunan, Peoples R China

[2] China Tobacco Hunan Ind Corp, R&D Ctr, Changsha 410014, Hunan, Peoples R China

[3] Honghe Univ, Coll Sci, Menzi 661100, Yunnan, Peoples R China

来源：

CHINA FUNCTIONAL MATERIALS TECHNOLOGY AND INDUSTRY FORUM | 2013年 / 320卷

基金：

高等学校博士学科点专项科研基金; 中国国家自然科学基金;

关键词：

(R)-1-(1H-indol-3-yl)propan-2-amines; Ellman's sulfonamides; ketones; condensation reaction; enantiopure; BUTANESULFINYL-PROTECTED AMINES; POT ASYMMETRIC-SYNTHESIS; SEROTONIN; TRYPTAMINES;

D O I：

10.4028/www.scientific.net/AMM.320.550

中图分类号：

TH [机械、仪表工业];

学科分类号：

0802 ;

摘要：

Two kinds of (R)-1-(1H-indol-3-yl)propan-2-amines were prepared through a five-step sequence procedure. The intermediate ketones were prepared by a modified Nef reaction using nitroalkenes to react with Fe-HCl. Condensation of (R)-(+)-2-methyl-2-propanesulfinamids with ketones, which was followed by a final desulfonation treatment with a solution of hydrochloride/methanol under mild conditions, optical pure (R)-sulfonamides could be synthesized. Without further chiral separation processing, the target products of (R)-1-(1H-indol-3-yl)propan-2-amines could be obtained with higher yield and excellent enantiopurity (over 99% e.e.), thus it was time-saving and cost-saving.

引用

页码：550 / +

页数：2

共 13 条

[1] One-pot asymmetric synthesis of tert-butanesulfinyl-protected amines from ketones by the in situ reduction of tert-butanesulfinyl ketimines [J].

Borg, G ;

Cogan, DA ;

Ellman, JA .

TETRAHEDRON LETTERS, 1999, 40 (37) :6709-6712

[2]

Glennon R. A. J., 1987, MED CHEM, V30, P1

[3] Novel and potent human and rat β3-adrenergic receptor agonists containing substituted 3-indolylalkylamines [J].

Harada, H ;

Hirokawa, Y ;

Suzuki, K ;

Hiyama, Y ;

Oue, M ;

Kawashima, H ;

Yoshida, N ;

Furutani, Y ;

Kato, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (07) :1301-1305

[4] Asymmetric synthesis of syn- and anti-1,3-amino alcohols [J].

Kochi, T ;

Tang, TP ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6518-6519

[5] CONVERSION OF NITRO PARAFFINS INTO ALDEHYDES AND KETONES [J].

KORNBLUM, N ;

ERICKSON, AS ;

KELLY, WJ ;

HENGGELER, B .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) :4534-4538

[6] Fe-HCl: An efficient reagent for deprotection of oximes as well as selective oxidative hydrolysis of nitroalkenes and nitroalkanes to ketones [J].

Pradhan, PK ;

Dey, S ;

Jaisankar, P ;

Giri, VS .

SYNTHETIC COMMUNICATIONS, 2005, 35 (07) :913-922

[7] Straightforward preparation of biologically active 1-aryl- and 1-heteroarylpropan-2-amines in enantioenriched form [J].

Rodriguez-Mata, Maria ;

Gotor-Fernandez, Vicente ;

Gonzalez-Sabin, Javier ;

Rebolledo, Francisca ;

Gotor, Vicente .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) :2274-2278

[8] THE SYNTHESIS OF TRYPTAMINES RELATED TO SEROTONIN [J].

SHAW, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (16) :4319-4323

[9] Psychedelic 5-Methoxy-N,N-Dimethyltryptamine: Metabolism, Pharmacokinetics, Drug Interactions, and Pharmacological Actions [J].

Shen, Hong-Wu ;

Jiang, Xi-Ling ;

Winter, Jerrold C. ;

Yu, Ai-Ming .

CURRENT DRUG METABOLISM, 2010, 11 (08) :659-666

[10] One-pot asymmetric synthesis of either diastereomer of tert-butanesulfinyl-protected amines from ketones [J].

Tanuwidjaja, Jessica ;

Peltier, Hillary M. ;

Ellman, Jonathan A. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (02) :626-629

← 1 2 →