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US 5,116,983 AGranted
Dehydrogenation process intermediates
AssigneeMerck & Co., Inc.
InventorsApurba Bhattacharya, Alan W. Douglas, Edward J. Grabowski, Ulf H. Dolling
Life of this patent
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Abstract
A process for dehydrogenating a compound of the formula ##STR1## which comprises reacting the compound with a silylating agent in the presence of a quinone to introduce a .DELTA..sup.1 double bond.
Claims6
The compounds of the formula ##STR23## wherein:
- Q is absent or is ##STR24## where R.sup.4 is methyl, C.sub.1-8 straight or branched chain alkyl, C.sub.3-6 cycloalkyl, phenyl, or combinations thereof;
- and R.sup.14 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 straight or branched chain alkoxy, halo, nitro or cyano;
- B is
- (a) when Q is present,. ##STR25## where X is NR.sup.1;
- and R.sup.1 is hydrogen, methyl or ethyl;
- (b) when Q is absent, ##STR26## where X' is N;
- (c) ##STR27## Z is (1) .beta.-hydrogen and .alpha.-hydroxyl;
- (2) .alpha.-hydrogen or .alpha.-hydroxyl and
- (a) ##STR28## where Alk is present or absent and is a straight or branched hydrocarbon chain of 1 to 12 carbon atoms;
- and R.sup.8 is,
- (i) hydrogen,
- (ii) hydroxyl,
- (iii) C.sub.1-12 alkyl
- (iv) NR.sup.9 R.sup.10, where R.sup.9 and R.sup.10 are each independently selected from hydrogen;
- C.sub.1-12 straight or branched chain alkyl;
- C.sub.1-12 straight or branched chain alkyl having a hydrogen substituted with a hydroxy, carboxylic acid or C.sub.1-4 alkyl ester;
- C.sub.3-6 cycloalkyl;
- phenyl;
- or R.sup.9 and R.sup.10 taken together with the nitrogen to which they are attached represent a 5-6 membered saturated ring comprising up to one other hereroatom selected from oxygen and nitrogen;
- or
- (v) OR.sup.11, where R.sup.11 is M, where M is hydrogen or alkali metal, or C.sub.1-18 straight or branched chain alkyl;
- benzyl;
- or
- (b) --(Alk)--OR.sup.12, where Alk is always present and has the same meaning as above;
- and
- R.sup.12 is
- (i) phenyl C.sub.1-6 alkylcarbonyl,
- (ii) C.sub.5-10 cycloalkylcarbonyl,
- (iii) benzoyl, or
- (iv) C.sub.1-18 alkoxycarbonyl;
- (v) amino, or C.sub.1-8 alkyl substituted amino, carbonyl;
- or
- (vi) hydrogen, provided that Alk is a branched C.sub.3 -C.sub.8 chain;
- (3) ##STR29## or.dbd.CH--Alk--OR.sup.12, where Alk is present or absent and has the same meaning as above, and R.sup.8 and R.sup.12 have the same meaning as above, and R.sup.12 is also hydrogen or C.sub.1-10 alkylcarbonyl;
- (4) ##STR30## where the dashed bond replaces the 17.alpha. hydrogen;
- (5) .alpha.-hydrogen and ##STR31## where R.sup.13 is, (a) C.sub.1-12 alkyl;
- or
- (b) NR.sup.9 R.sup.10 ;
- (6) .alpha.-hydrogen and cyano;
- or
- (7) .alpha.-hydrogen and tetrazolyl;
- R' is hydrogen or methyl;
- R" is hydrogen or .beta.-methyl;
- R"' is hydrogen, .beta.-methyl or hydroxyl.
41 more elements
Dependencies are inferred from the claim text.