o-Fluorobenzaldehyde → Methyl 1-(2-fluorobenzyl)-5-methylpiperidine-3-carboxylate

HRID 594938Notes

Reaction equation

HRID 594938 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCl>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][N:6]1[CH2:7][CH:2]([CH3:1])[CH2:3][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:5]1

Participants

6

Reactant 3

HCID 67970o-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18404439Methyl 5-methylpiperidine-3-carboxylate

Product 1

HCID 66800957Methyl 1-(2-fluorobenzyl)-5-methylpiperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flask, dichloromethane (8 mL) and acetic acid (8 drops) was added to methyl 5-methylpiperidine-3-carboxylate (300 mg, 1.9 mmol) and 2-fluorobenzaldehyde (3.8 mmol). The reaction was stirred for 15 minutes. Sodium triacetoxyborohydride (1.6 g, 7.6 mmol) was added in one portion. The reaction was stirred overnight. The reaction was concentrated in vacuo and purified using prep LC/MS.

Workup

  1. stirringThe reaction was stirred overnight
  2. concentrationThe reaction was concentrated in vacuo
  3. custompurified

Sources & evidence

ORD record
ord-494fa08c152f49ff9bc8fe57174f2d32
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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