Acetic Acid → 4-Piperidinecarboxylic acid

HRID 2403229Notes

Reaction equation

HRID 2403229 reaction equation
C([BH3-])#N.[Na+].C1(N2[C:15]([CH:16]3CCC[O:17]3)=[C:14]([C:21]3ON=[C:23]([C:26]4C=CC(C=O)=CC=4)[N:22]=3)C=N2)CCCCC1.C(O)(=[O:36])C>CO>[NH:22]1[CH2:21][CH2:14][CH:15]([C:16]([OH:17])=[O:36])[CH2:26][CH2:23]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 86663317HCID 86663317, compound

Product 1

HCID 37734-Piperidinecarboxylic acidYield 200%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (17.3 mg; 0.275 mmol) was added to a solution of 4-(5-(1-cyclohexyl-5-(tetrahydrofuran-2-yl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde (99 mg; 0.25 mmol), obtained from step 2, and isonipecotic acid (64.6 mg; 0.50 mmol) in methanol (3 mL) and acetic acid (45 μL; 0.75 mmol) and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the crude material purified by reverse phase preparative HPLC to give Example 125 as a white solid. 1H NMR: (DMSO-d6, 400 MHz) δ 8.20 (1 H, s), 8.04 (2 H, d, J=8.0 Hz), 7.54 (2 H, d, J=8.0 Hz), 5.72 (1 H, dd, J=9.5, 6.9 Hz), 4.47 (1 H, d, J=8.2 Hz), 4.16 (1 H, q, J=7.5 Hz), 3.97 (1 H, q, J=7.5 Hz), 3.57 (2 H, s), 2.79 (2 H, d, J=10.9 Hz), 2.55-2.50 (1 H, m), 2.26-2.13 (3 H, m), 2.11-1.78 (11 H, m), 1.72 (1 H, d, J=12.5 Hz), 1.65-1.52 (2 H, m), 1.50-1.35 (2 H, m), 1.35 (1 H, m). LC/MS: 506 (M+H)+. HPLC (Method B) Rt 2.77 min (Purity: 99.2%).

Sources & evidence

ORD record
ord-10b4d356a9894bdabf55d9265e77e0cd
Source dataset
uspto-grants-2014_08
Patent number
US08802663B2

Reaction notes

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