Got another one for you guys. I was unable to locate any useful procedures on the preparation on pyrrolidine. Plain pyrrolidine that is, no substituted. The best idea I can come up with is pyrrole ----> pyrrolidine through catalytic hydrogenation, or sodium/ethanol. Through further reading, it looked as if pyrrolidine can accidentally be reduced further into butylamine, but I could have misinterpreted. Does anyone have any fresh ideas on this one?
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Douchermann
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no1uno
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Langheld supposedly came up with a pyrrolidine from the hypochlorite/strecker oxidation of l-Proline if that is any help
Enkidu
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You mean decarboxylation?
no1uno
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Dunno if you mean me Enkidu, but if you do - Langheld & Dakin, amongst others, did the work on the hypohalite/chloramine "Strecker" degradations of the various amino acids - when they applied the same to histidine & proline, they got unexpected results in some circumstances. Love reading these "fuckups", makes me feel better
Enkidu
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I can't say for sure by what mechanism the reaction of proline with a hypochlorite proceeds. A little quick looking tells me that the products are uncertain. I can tell you that the Strecker degradation produces an aldehyde (edit: or a ketone). Check the mechanism. So it's better to call it a decarboxylation if it produces pyrrolidine
no1uno
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An attempted Strecker would probably be more appropriate, least the olden day author's tell us about the fuckups huh?
Douchermann
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I'm siding with enkidu on this one; I don't know if strecker is the appropriate name of the reaction you might be speaking of. Would you care to post any references or instances of experimentation? BTW, thanks for pointing me in the direction of proline - didn't even think to look through amino acids.
Enkidu
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An attempted Strecker would probably be more appropriate, least the olden day author's tell us about the fuckups huh?
One man's trash is another mans treasure
no1uno
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Ain't that the bloody truth - IIRC with Langheld-Strecker degradations, you need at LEAST 2 equivalents of hypochlorite to substrate or you will get the prettiest red (rapidly becoming reddish-brown) tar you've ever fucking seen
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