Acetic Acid → 4-Piperidinecarboxylic acid

HRID 2403224Notes

Reaction equation

HRID 2403224 reaction equation
C([BH3-])#N.[Na+].C1(N2[C:15]([CH2:16][O:17]C)=[C:14]([C:19]3ON=[C:21]([C:24]4C=CC(C=O)=CC=4)[N:20]=3)C=N2)CCCCC1.C(O)(=[O:34])C>CO>[NH:20]1[CH2:19][CH2:14][CH:15]([C:16]([OH:17])=[O:34])[CH2:24][CH2:21]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 86663314HCID 86663314, compound

Product 1

HCID 37734-Piperidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (32.5 mg; 0.517 mmol) was added to a solution of 4-(5-(1-cyclohexyl-5-(methoxymethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde, obtained from step 1, (172 mg; 0.47 mmol) and isonipecotic acid (121.4 mg; 0.94 mmol) in a mixture of methanol (3 mL) and acetic acid (80.7 μl; 0.141 mmol) and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue purified by preparative HPLC to give Example 64 as a white solid. 1H NMR (DMSO-d6) δ 8.23 (1 H, s), 8.04 (2 H, d, J=8.1 Hz), 7.54 (2 H, d, J=8.0 Hz), 5.02 (2 H, s), 4.44-4.34 (1 H, m), 3.56 (2 H, s), 3.34 (3 H, s), 2.78 (2 H, d, J=11.0 Hz), 2.26-2.17 (1 H, m), 2.06 (2 H, t, J=11.2 Hz), 1.96-1.76 (8 H, m), 1.71 (1 H, d, J=12.8 Hz), 1.66-1.52 (2 H, m), 1.53-1.37 (2 H, m), 1.25 (1 H, t, J=13.0 Hz). LC/MS: 480 (M+H)+. HPLC (Method G) Rt=2.39 min (Purity: 96.7%).

Sources & evidence

ORD record
ord-d9339b1d71b14cad84b1696a0c05f6ad
Source dataset
uspto-grants-2014_08
Patent number
US08802663B2

Reaction notes

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