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Processes and intermediates for cis or trans 2- or 3-(1-acyl-3-vinyl-4-piperidine)acetic or propionic acid esters
| Details |
Inventors: Grethe, Guenter; Uskokovic, Milan Radoje;
Assignee: Hoffmann-La Roche Inc. (Nutley, NJ)
Primary Examiner: Todd; G. Thomas
Assistant Examiner:
Attorney, Agent or Firm: Welt; Samuel L., Gould; George M., Isgro; William G.
Cis or trans 2-(1-acyl-3-vinyl-4-piperidine)acetic acid esters and cis or trans 3-(1-acyl-3-vinyl-4-piperidine)propionic acid esters, antipodes and racemates thereof, are prepared, inter alia, from the corresponding cis or trans 2- or 3-[1-acyl-3-(2-chloroethyl)-4-piperidine]acetic or propionic acid esters, respectively. The cis or trans 2- or 3-(1-acyl-3-vinyl-4-piperidine)acetic or propionic acid esters are useful as intermediates for the synthesis of quinine and quinidine and analogs and stereoisomers thereof. |
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DETAILED DESCRIPTION We claim: 1.
A process for the preparation of cis or trans 2-(1-acyl-3-vinyl-4-piperidine)acetic acids or esters, antipodes or racemates thereof or cis or trans 3-(1-acyl-3-vinyl-4-piperidine) propionic acids or esters or antipodes or racemates thereof which comprises the steps of: a.
treating the corresponding cis or trans 2- or 3-(3-ethyl-4-piperidine)acetic or propionic acid or ester, antipode or racemate thereof with a chlorinating agent; b.
irradiating the product of step (a) i.
e.
, cis or trans 2- or 3-(1-chloro-3-ethyl-4-piperidine)acetic or propionic acid or ester, antipode or racemate thereof; c.
treating the product of step (b), i.
e.
, cis or trans 2- or 3-[3-(2-chloroethyl)-4-piperidine]acetic or propionic acid or ester, antipode or racemate thereof, with an acid chloride; d.
treating the product of step (c), i.
e.
, cis or trans 2- or 3-[1-acyl-3-(2-chloroethyl)-4-piperidine]acetic or propionic acid or ester, antipode or racemate thereof, with an alkali metal iodide; and e.
treating the product of step (d), i.
e.
, cis or trans 2- or 3-[1-acyl-3-(2-iodoethyl)-4-piperidine]acetic or propionic acid or ester, antipode or racemate thereof, with an organic base or inorganic salt to yield the desired end product.
2.
A process for the preparation of cis or trans 2-(1-acyl-3-vinyl-4-piperidine)acetic acid esters, antipodes or racemates thereof or cis or trans 3-(1-acyl-3-vinyl-4-piperidine) propionic acid esters or antipodes or racemates thereof which comprises the steps of: a.
treating the corresponding cis or trans 2- or 3-(3-ethyl-4-piperidine)acetic or propionic acid ester, antipode or racemate thereof with a chlorinating agent; b.
irradiating the product of step (a), i.
e.
, cis or trans 2- or 3-(1-chloro-3-ethyl-4-piperidine)acetic or propionic acid ester, antipode or racemate thereof; c.
treating the product of step (b), i.
e.
, cis or trans 2- or 3-[3-(2-chloroethyl)-4-piperidine]acetic or propionic acid ester, antipode or racemate thereof, with an acid chloride; d
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