2-Fluoro-6-methoxybenzaldehyde → HCID 67515938, compound

HRID 1465728Notes

Reaction equation

HRID 1465728 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][NH:7][CH2:6][CH:5]([C:9]([O:11][CH3:12])=[O:10])[CH2:4]1.[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:15]=1[CH:16]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:15]=1[CH2:16][N:7]1[CH2:8][CH:3]([O:2][CH3:1])[CH2:4][CH:5]([C:9]([O:11][CH3:12])=[O:10])[CH2:6]1

Participants

6

Reactant 3

HCID 27373572-Fluoro-6-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67033617Methyl 5-methoxypiperidine-3-carboxylate

Product 1

HCID 67515938HCID 67515938, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To Methyl 5-methoxypiperidine-3-carboxylate (500 mg, 2.9 mmol) in DCM (10 mL) was added 2-fluoro-6-methoxybenzaldehyde (890 mg, 5.8 mmol) and 10 drops of acetic acid. After stirring for 15 min, sodium triacetoxyborohydride (2.4 g, 11.6 mmol) was added. The reaction mixture was stirred at room temperature overnight. After quench with saturated Na2CO3, the mixture was extracted with DCM. Dried and concentrated to give crude product.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customAfter quench with saturated Na2CO3
  3. extractionthe mixture was extracted with DCM
  4. customDried
  5. concentrationconcentrated
  6. customto give crude product

Sources & evidence

ORD record
ord-673236604f954cc2a5b3857878a0ce2b
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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