Convenient and inexpensive synthesis of (1R,2R)-trans-1-amino-6-nitroindan- 2-ol

Advanced Synthesis and Catalysis

Volumn 347, Issue 2-3, 2005, Pages 255-265

  Kozhushkov, Sergei I ^a   Yufit, Dmitrii S ^b   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

Amino alcohols; Aromatic substitution; Chiral resolution; Indene; Nitration; Structure elucidation

Indexed keywords

1 AMINO 6 NITROINDAN 2 OL; INDAN DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; NITRATION; QUANTITATIVE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 15044362464     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404296     Document Type: Article

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74. Cheapest commercial source: Alfa Aesar, US $ 370.00 for 2.5 kg.
75. 2O] and CCDC-250617 [(1R,2R)-10] with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (+44)1223-336-033; E-mail: deposit@ccdc.cam.ac.uk].
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77. Cheapest commercial sources: a) Senn Chemicals AG, US $ 583.00 for 1 kg; b) ChemPacific USA Sales Marketing and Research Center, US $ 880.00 for 1 kg, US $ 3,200.00 for 5 kg, bulk available.
78. Cheapest commercial sources: a) Senn Chemicals AG, US $ 583.00 for 1 kg; b) ChemPacific USA Sales Marketing and Research Center, US $ 880.00 for 1 kg, US $ 3,200.00 for 5 kg, bulk available.
79. B. M. Trost, Science 1991, 254, 1471-1477.
80. Cheapest commercial sources: a) Pfaltz&Bauer, Inc., US $ 62.35 for 1 kg; b) Acrōs Organics, US $ 71.70 for 1 kg; c) City Chemical LLC, US $ 38.50 for 1 kg.
81. Cheapest commercial sources: a) Pfaltz&Bauer, Inc., US $ 62.35 for 1 kg; b) Acrōs Organics, US $ 71.70 for 1 kg; c) City Chemical LLC, US $ 38.50 for 1 kg.
82. Cheapest commercial sources: a) Pfaltz&Bauer, Inc., US $ 62.35 for 1 kg; b) Acrōs Organics, US $ 71.70 for 1 kg; c) City Chemical LLC, US $ 38.50 for 1 kg.
83. Cheapest commercial sources: a) Oakwood Products, Inc., US $ 62.00 for 1 kg; b) City Chemical LLC, US $ 109.00 for 2.5 kg; c) Fluorochem Ltd., £ 95.00 for 5 kg.
84. Cheapest commercial sources: a) Oakwood Products, Inc., US $ 62.00 for 1 kg; b) City Chemical LLC, US $ 109.00 for 2.5 kg; c) Fluorochem Ltd., £ 95.00 for 5 kg.
85. Cheapest commercial sources: a) Oakwood Products, Inc., US $ 62.00 for 1 kg; b) City Chemical LLC, US $ 109.00 for 2.5 kg; c) Fluorochem Ltd., £ 95.00 for 5 kg.
86. [10e] respectively. However, this decreases the yield to 85 and 82.5%, respectively, as rac-8 is rather well soluble in both solvents. Moreover, the main impurity - succinimide - remains even after recrystallization (from traces and up to 5%). As this impurity is very poorly soluble in diethyl ether, we have slightly modified the procedure in this point.
87. 1H NMR spectrum. Unlike this, the extraction with tert-butyl methyl ether proceeds at a lower temperature and without undesirable side reactions.
88. 4 by atmospheric moisture only.
89. The recovery of (-)-dibenzoyl L-tartrate has been described in the patents: a) S. Martin, D. Piergentili, UK Pat. Appl. GB 2382074 A1, 2003; Chem. Abstr. 2003, 138, 385169; b) J. Jendrichovsky, L. Stibranyi, Recovery of (+)- and (-)-dibenzoyltartaric acid monohydrate after resolution of optically active forms of a-methyl-β-dimethylaminopropiophenone. Czech. Patent, 1975; Chem. Abstr. 1975, 83, 78879. However, these patents do not cover our method, as in both patents the substituted tartaric acid derivatives from the resolution process were firstly neutralized by adding a base (for example, aqueous sodium bicarbonate), extracted into an aqueous phase, and secondly crystallized from the aqueous phase by addition of a mineral acid.
90. The recovery of (-)-dibenzoyl L-tartrate has been described in the patents: a) S. Martin, D. Piergentili, UK Pat. Appl. GB 2382074 A1, 2003; Chem. Abstr. 2003, 138, 385169; b) J. Jendrichovsky, L. Stibranyi, Recovery of (+)- and (-)-dibenzoyltartaric acid monohydrate after resolution of optically active forms of a-methyl-β-dimethylaminopropiophenone. Czech. Patent, 1975; Chem. Abstr. 1975, 83, 78879. However, these patents do not cover our method, as in both patents the substituted tartaric acid derivatives from the resolution process were firstly neutralized by adding a base (for example, aqueous sodium bicarbonate), extracted into an aqueous phase, and secondly crystallized from the aqueous phase by addition of a mineral acid.
91. 2O can have a dark color.
92. [24]
93. 20: +45.3 (c 1.672, MeOH) and +47.0 (c 2.088, MeOH), respectively), the progress of purification can better be monitored by measuring the melting points. The second salt is better soluble in EtOH and in THF than the first one.
94. [1]