Triethylamine → Methyl 1-(pyridin-2-ylmethyl)piperidine-2-carboxylate

HRID 1791357Notes

Reaction equation

HRID 1791357 reaction equation
Cl.[NH:2]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:3]1[C:4]([O:6][CH3:7])=[O:5].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C>[CH3:7][O:6][C:4]([CH:3]1[CH2:8][CH2:9][CH2:10][CH2:11][N:2]1[CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1)=[O:5]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 142732-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 13246231Methyl Pipecolinate Hydrochloride

Product 1

HCID 11776206Methyl 1-(pyridin-2-ylmethyl)piperidine-2-carboxylateYield 93.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Methyl pipecolinate hydrochloride (9.0 g, 50 mmol) was mixed with pyridine-2-carbaldehyde (5.4 g, 50 mmol) and triethylamine (5.05 g, 50 mmol) in dichloroethane (180 mL) at room temperature. Sodium triacetoxyborohydride (14.8 g, 70 mmol) was added in one portion. After the reaction mixture was stirred at room temperature for 1.5 h, saturated sodium carbonate was added. Then the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated to give 10.9 g (93.6%) of the title compound as a pale brown oil. 1H NMR (CDCl3), δ(ppm): 8.53 (d, 1H), 7.65 (td, 1H), 7.49 (d, 1H), 7.14 (t, 1H), 3.89 (d, 1H), 3.73 (s, 3H), 3.68 (d, 1H), 3.25 (dd, 1H), 2.97 (m, 1H), 2.25 (m, 1H), 1.85 (m, 2H), 1.30-1.76(m, 4H).

Workup

  1. extractionThen the mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c969145559604c7d8937ea3bf6a22d15
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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