Production of N-substituted...

Details Production of N-substituted... Production of N-substituted...

2006-03-07

2006-03-07

Price, Elvis O. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

Reexamination Certificate

active

07009078

ABSTRACT:
From compounds of formula IIwherein R1and R2are independently of one another H, C1–C6alkyl, C1–C6halogenalkyl, C1–C6alkoxy, C1–C6alkoxy-C1–C6alkyl, or C1–C6alkoxy-C1–C6alkyloxy, R3is C1–C6alkyl, R4is C1–C6alkyl, and R5is C1–C6alkyl, C1–C6hydroxyalkyl, C1–C6alkoxy-C1–C6-alkyl, C1–C6alkanoyloxy-C1–C6alkyl, C1–C6aminoalkyl, C1–C6alkylamino-C1–C6-alkyl, C1–C6-dialkylamino-C1–C6-alkyl, C1–C6-alkanoylamido-C1–C6-alkyl, HO(O)C—C1–C6-alkyl, C1–C6alkyl-O—(O)C—C1–C6alkyl, H2N—C(O)—C1–C6alkyl, C1–C6alkyl-HN—C(O)—C1–C6alkyl or (C1–C6alkyl)2N—C(O)—C1–C6-alkyl, R6is C1–C6alkyl, R7is C1–C6alkyl or C1–C6alkoxy, or R6and R7together are tetramethylene, pentamethylene, 3-oxa-1,5-pentylene or —CH2CH2O— substituted, if necessary, with C1–C4-Alkyl, phenyl or benzyl, it is possible—through halolactonization, azidation of the halogen group, ring opening with an amine R5—NH2, and reduction of the azide group to form the amino group—to prepare compounds of formula Iwherein R5is C1–C6alkyl, C1–C6hydroxyalkyl, C1–C6alkoxy-C1–C6alkyl, C1–C6alkanoyloxy-C1–C6alkyl, C1–C6aminoalkyl, C1–C6alkylamino-C1–C6alkyl, C1–C6dialkylamino-C1–C6-alkyl, C1–C6alkanoylamido-C1–C6alkyl, HO(O)C—C1–C6alkyl, C1–C6alkyl-O—(O)C—C1–C6alkyl, H2N—C(O)—C1–C6alkyl, C1–C6alkyl-HN—C(O)—C1–C6alkyl or (C1–C6alkyl)2—N—C(O)—C1–C6alkyl. If 2(S), 7(R)-diastereomer of formula II is used, the 2(S), 4(S), 5(S), 7(S)-diastereomer of formula Iais obtained in a high degree of purity.

REFERENCES:
patent: 0678503 (1995-10-01), None
Herold et al, JOC 1989, vol. 54 (5) pp 1178-1185.
Cahiez et al, Synthesis, 1998, pp1199-1200
Herold et al, J O C 1989, 54(5) pp. 1178-1185.

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