Production of tertiary amines by reductive amination

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

06949642

ABSTRACT:
A process for the production of tertiary amines by reductive amination of carbonyl compounds with secondary amines in the presence of a water scavenger, preferably trifluoroacetic acid anhydride, is disclosed. This process has applications in the preparation of imidazole-containing benzodiazepines, which are inhibitors of farnesyl protein transferase.

REFERENCES:
patent: 6100395 (2000-08-01), Chen et al.
patent: 6458783 (2002-10-01), Ding et al.
patent: 150857 (1990-11-01), None
de Villepin et al, “Etude par Spectrophotometrie Infrarouge des Interactions entre l'Eau et Quelques Acides Monocarboxyliques en Solution dans le Tetrachlorure de Carbone” Annales de Chemie, tome 1 (9-10), pp. 365-376 (1966). English Translation.
Black and DiCesare Investigations into the Mechanism of the Titanium Isopropoxide Catalyzed Reductive Amination Reaction Book of Abstracts, 213 ACS National Meeting, San Francisco, Apr. 13-17. CHED-580 American Chemical Society: Wasington DC (1997).
de Villepin et al, “Etude par Spectrophotometrie Infrarouge des Interactions entre l'Eau et Quelques Acides Monocarboxyliques en Solution dans le Tetrachlorure de Carbone” Annales de Chemie, tome 1 (9-10), pp. 365-376 (1966).
U.S. Provisional Application No. 60/115,587 (Chen et al) filed Jan. 12, 1999.
Borg, G. et al. “One-pot asymmetric synthesis oftert-butanesulfinyl-protected amines from ketones by the in situ reduction oftert-butanesulfinyl ketimines”; Tetrahedron Letters, 40: 6709-6712 (1999).
Borg, G. et al. “Asymmetric synthesis of amines and a,a-disubstituted amino acids from tert-butanesulfinyl ketimines”; Book of Abstracts, 219th ACS National Meeting (2000) [Abstract].
Liu, G. et al. “Synthesis of Enantiomerically PureN-tert-Butanesulfinyl Imines (tert-Butanesulfinimines) by the Direct Condensation oftert-Butanesulfinamide with Aldehydes and Ketones”; J. Org. Chem. 64: 1278-1284 (1999).
Loh, T. et al. “A Highly Stereoselective One-Pot Asymmetric Synthesis of Homoallylic Amines and Amino Acids From Aldehydes”; Tetrahedron Letters, 38(5): 865-868 (1997).
Pollard, C.B. et al. “The mechanism of the Leuckart reaction”; J. Org. Chem. 16: 661-672 (1951).
Elderfield, R.C. “Study of the synthesis of plasmochin by the reductive amination method with Raney nickel”; J. Am. Chem. Soc., 70: 40-44 (1948).
Form PCT/ISA/220 (Apr. 2002); International Search Report of PCT/US02/11942, filed Apr. 12, 2002; mailed Dec. 23, 2002.

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

Production of tertiary amines by reductive amination does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Production of tertiary amines by reductive amination, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Production of tertiary amines by reductive amination will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3434960

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