Acetic Acid → HCID 86719574, compound

HRID 2208908Notes

Reaction equation

HRID 2208908 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH:21](=O)[CH3:22].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:21][CH3:22])[CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70873982HCID 70873982, compound

Product 1

HCID 86719574HCID 86719574, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of methyl 5-chloro-2-methyl-3-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzoate (0.40 g, 1.35 mmol) and acetaldehyde (0.120 g, 2.71 mmol) in dichloroethane (5 mL), acetic acid (0.48 g, 8.1 mmol) was added and the reaction stirred at room temperature for 10 minutes. Then sodium triacetoxyborohydride (0.663 g, 4.05 mmol) was added at 0° C. and the reaction stirred for 3 h at room temperature. On completion, the solvent was removed under reduced pressure and the crude material purified by column chromatography to the title compound (0.38 g, 86%).

Workup

  1. stirringthe reaction stirred for 3 h at room temperature
  2. customOn completion, the solvent was removed under reduced pressure
  3. customthe crude material purified by column chromatography to the title compound (0.38 g, 86%)

Sources & evidence

ORD record
ord-b7ba0913df474089afbc378c9dfd493e
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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