Acetyl chloride → HCID 67071433, compound

HRID 874256Notes

Reaction equation

HRID 874256 reaction equation
[C:1](Cl)(=O)C.[CH3:5][O:6][C:7](=[O:33])/[CH:8]=[CH:9]/[C:10]1[CH:11]=[C:12]2[C:29](=[CH:30][CH:31]=1)[O:28][C:15]1([CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23]C(C)(C)C)=O)[CH2:16]1)[CH2:14][C:13]2=[O:32]>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:33])/[CH:8]=[CH:9]/[C:10]1[CH:11]=[C:12]2[C:29](=[CH:30][CH:31]=1)[O:28][C:15]1([CH2:20][CH2:19][CH2:18][N:17]([C:21](=[O:23])[CH3:1])[CH2:16]1)[CH2:14][C:13]2=[O:32]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 67071461HCID 67071461, compound2×

Product 1

HCID 67071433HCID 67071433, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (168 mg, 2.14 mmol) was added dropwise to a stirred solution of (±)-(E)-3-[4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (Intermediate 2, 600 mg, 1.78 mmol) and TEA (0.742 ml, 5.33 mmol) in DCM (30 ml). The resulting mixture was stirred overnight at RT, then washed with 5% NaHCO3, brine and dried over Na2SO4. The crude mixture was purified by column chromatography (eluent: DCM/MeOH 99:1) to give (±)-(E)-3-[1′-acetyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (609 mg).

Workup

  1. washwashed with 5% NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customThe crude mixture was purified by column chromatography (eluent: DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-ce882998796743d6bb658dd375a7592b
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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