Pyridoxal 5'-phosphate → tert-butyl 2-aminopiperidine-1-carboxylate

HRID 1919271Notes

Reaction equation

HRID 1919271 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.C1C=[N+:31]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.N[C@H](C(O)=O)C.CC1N=CC(COP(O)(O)=O)=C(C=O)C=1O.[OH-].[Na+]>>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[NH2:31])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 6

HCID 1051Pyridoxal 5'-phosphateHCID 5893Nadide (JAN/USAN/INN)HCID 5950L-AlanineHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

Product 1

HCID 4112359tert-butyl 2-aminopiperidine-1-carboxylate

Procedure

To a flask containing 0.6 g of a substrate N-Boc-3-piperidinone, 0.82 g of D-glucose, 4 mg of NAD+, 1.62 g of L-alanine, and 4.0 mg of pyridoxal phosphate, a culture fluid of the recombinant E. coli HB101 (pNTPSPAG), obtained in Example 10, which expresses TPS, PALDH, and GDH was added so that total volume was 30 ml. The resultant product was stirred at 30° C. for 20 hours while being adjusted to a pH of 6.8 by drippage of 5 N aqueous solution of sodium hydroxide. The amount of N-Boc-aminopiperidine produced and the optical purity thereof were measured according to the method described in Example 19. In the result, the amount produced was 0.54 g. The absolute configuration of N-Boc-aminopiperidine was (S), and the optical purity was 99.4% e.e.

Workup

  1. custom(pNTPSPAG), obtained in Example 10, which
  2. additionwas added so that total volume was 30 ml

Sources & evidence

ORD record
ord-0d44b2af5d6a4911b01d20c5c4d4e38e
Source dataset
uspto-grants-2012_05
Patent number
US08168412B2

Reaction notes

Loading…