Pyridoxal 5'-phosphate → 1-BOC-3-Aminopiperidine
Reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[NH2:27][C@H](C(O)=O)C.CC1N=CC(COP(O)(O)=O)=C(C=O)C=1O>>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH2:27])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]Participants
Procedure
After two hours in reaction, 1.25 g of N-Boc-3-piperidinone, 1.7 g of D-glucose, 1.0 g of L-alanine, and 3.3 mg of pyridoxal phosphate were added. Further, after five hours in reaction, 1.25 g of N-Boc-3-piperidinone, 1.7 g of D-glucose, and 3.3 mg of pyridoxal phosphate were added. During the reaction, the reaction liquid was sampled. From the sample, N-Boc-3-aminopiperidine was extracted by the addition of ethyl acetate after basifying the sample with 6 N aqueous solution of sodium hydroxide. The amount of N-Boc-3-aminopiperidine produced was measured by analyzing N-Boc-3-aminopiperidine under the following GC conditions. Further, by the law of the art, N-Boc-3-aminopiperidine thus obtained was acted on by 3,5-dinitrobenzyl chloride to form a dinitrobenzyl derivative. After that, the dinitrobenzyl derivative was analyzed under the following HPLC conditions, whereby the optical purity thereof was measured. In the result, the amount of N-Boc-3-aminopyrrolidine produced after 23.5 hours in reaction was 3.13 g. The absolute configuration of N-Boc-3-aminopyrrolidine was (S), and the optical purity was not less than 99.9% e.e.
Workup
- additionwere added
- additionwere added
- customDuring the reaction
- customthe reaction liquid
- aliquotwas sampled
- extractionFrom the sample, N-Boc-3-aminopiperidine was extracted by the addition of ethyl acetate
Sources & evidence
- ORD record
- ord-1312f71c753a4459809e1a841e31ad84
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168412B2
Reaction notes
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