Reduction of indole compounds to indoline compounds

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

260315, 2603269, 562605, 2603473, C07D20904, C07D20994, C07D48704

Patent

active

042105900

ABSTRACT:
A method for reducing indole compounds to the corresponding indoline compounds substantially free of undesirable side reactions is described. The method involves contacting an indole compound with a borane complex reagent in the presence of trifluoroacetic acid. The method is rapidly and readily carried out and provides an excellent method for preparing certain indoline compounds from the corresponding indole compounds. A novel dioxyborane useful as a borane reagent is also disclosed.

REFERENCES:
patent: 2569415 (1956-09-01), Hartmann et al.
patent: 3329619 (1967-07-01), Hudson et al.
patent: 3657254 (1972-04-01), Barkov et al.
patent: 3853878 (1974-12-01), Jonas et al.
patent: 3980797 (1976-09-01), Jonas et al.
Lane et al., J. Org. Chem. 39, 3052-3054 (1971).
Yoon et al., J. Org. Chem. 38, 2786-2792 (1973).
Brown et al., J. Am. Chem. Soc. 92 (6), 1637-1646 (1970).
Pelter et al., Chem. Comm., 1970, pp. 347-348.
Lane, Chem. Reviews 76, 773-779 (1976).
Littell et al., J. Org. Chem. 38, 1504-1510 (1973).
Kikugawa et al., J. Chem. Research (S), 212-213 (1977).
Berger et al., J. Med. Chem. 20, 600-601 (1977).
Brown et al., J. Am. Chem. Soc. 93 (7), 1816-1818 (1978).
Aldrich Catalog of Organic Chemicals, 1977-1978, pp. 109-110, 159.
Alfa/Ventron Catalog, pp. 6-9.
J. Organic Chem. 12/9/77 issue, back cover.
Kabalka et al., J. Org. Chem. 42, 512-517 (1977).
Robinson, Chem. Reviews 69, 785-797 (1969).
Brown et al., J. Am. Chem. Soc. 82, 681-686 (1960).
Gribble et al., J. Am. Chem. Soc. 96, 812-814 (1974).
Berger et al., Tetrahedron Letters, Nos. 22-23, 1807 (1975).
Monti et al., Tetrahedron 27, 3331-3339 (1971).
Plieninger et al., Liebig's Annalen Chem., 680, 69, 74-75 (1964).
Berger, Synthesis, 508-510 (1974).
Feuer et al., J. Org. Chem. 34, 1817-1821 (1969).
Brown et al., J. Am. Chem. Soc. 99, 25, 8218-8226 (1977).
Gribble et al., Synthesis, pp. 859-860 (1977).
Kikugawa, J. Chem. Research (S), 184-185 (1978).
Maryanoff et al., J. Org. Chem. 43, No. 13, 2733-2755 (1978).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Reduction of indole compounds to indoline compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Reduction of indole compounds to indoline compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Reduction of indole compounds to indoline compounds will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-298054

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.