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US 2009/0155862 A1Published application
Process for the preparation of 2-hydroxymethyl-pyrrolidine-3,4-diols
OwnerUlrich KAMPFEN, Eva Maria URBAN +2inventors
InventorsUlrich KAMPFEN, Eva Maria URBAN, Claus JESSEN, Martin CLAUSEN
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Abstract
A process for the preparation of 2-hydroxymethyl-pyrrolidine-3,4-diols of the formulae: including the steps of: a) bioxidation of N-protected aminotetraols of the formula: b) deprotection of the corresponding 5-amino-5-deoxy-pentulose of the formula: and c) hydrogenation of the corresponding 5-amino-5-deoxy-pentulose of the formula:
Claims44
A process comprising the steps of:
- a) oxidizing an N-protected aminotetraol of the formula:
- or a salt thereof, wherein R1 is H, substituted or unsubstituted C1-4-alkyl, substituted or unsubstituted C2-4-alkenyl or OR2, R2 being unsubstituted C1-4-alkyl, with a microorganism or a cell-free extract thereof to yield the corresponding N-protected-5-amino-5-deoxy-pentulose of formula:
- R1 being defined as above,
- b) removing N-protective group of said N-protected 5-amino-5-deoxypentulose (II) to yield the corresponding 5-amino-5-deoxy-pentulose of formula:
- and
- c) catalytically hydrogenating said 5-amino-5-deoxy-pentulose (III) to produce the corresponding (2R)- and/or (2S)-hydroxymethyl-pyrrolidine-3,4-diol of formula:
3 more elements
The process comprising the steps of:
- a) removing the N-protective group of N-protected 5-amino-5-deoxy-pentulose of the formula:
- wherein R1 is, substituted or unsubstituted C1-4-alkyl, substituted or unsubstituted C2-4-alkenyl CR2, R2 being unsubstituted C1-4-alkyl, under alkaline conditions to yield corresponding 5-amino-5-deoxy-pentulose of formula:
- and
- b) catalytically hydrogenating said 5-amino-5-deoxy-pentulose (III) to produce corresponding (2R)- and/or (S)-2-hydroxymethyl-pyrrolidine-3,4-diol of formula:
1 more element
18-23. (canceled)
N-Formyl-1-amino-1-deoxy-L-arabinitol of formula:
N-Formyl-1-amino-1-deoxy-L-arabinitol of formula:
Dependencies are inferred from the claim text.