Ethyl isocyanate → HCID 66932624, compound

HRID 2046731Notes

Reaction equation

HRID 2046731 reaction equation
[CH2:1]([N:3]=C=O)[CH3:2].[CH3:6][O:7][C:8](=[O:34])/[CH:9]=[CH:10]/[C:11]1[CH:12]=[C:13]2[C:30](=[CH:31][CH:32]=1)[O:29][C:16]1([CH2:21][CH2:20][N:19]([C:22](OC(C)(C)C)=[O:23])[CH2:18][CH2:17]1)[CH2:15][C:14]2=[O:33]>C(Cl)Cl>[CH3:6][O:7][C:8](=[O:34])/[CH:9]=[CH:10]/[C:11]1[CH:12]=[C:13]2[C:30](=[CH:31][CH:32]=1)[O:29][C:16]1([CH2:17][CH2:18][N:19]([C:22](=[O:23])[NH:3][CH2:1][CH3:2])[CH2:20][CH2:21]1)[CH2:15][C:14]2=[O:33]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 52952087(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester2×

Product 1

HCID 66932624HCID 66932624, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (0.185 ml, 1.33 mmol) and ethylisocyanate (38 mg, 0.53 mmol) were added to a suspension of (E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester hydrochloride (150 mg, 0.44 mmol, Intermediate 1) in DCM (4 ml), and the mixture was stirred at RT for 1.5 h. The mixture was partitioned between aqueous NaHCO3 (saturated solution) and DCM and the organic phase was dried over Na2SO4 and evaporated. The crude product was purified by column chromatography (eluent:DCM/MeOH/NH4OH 97:3:0.3) to give (E)-3-{1′-ethylcarbamoyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (150 mg).

Workup

  1. customThe mixture was partitioned between aqueous NaHCO3 (saturated solution) and DCM
  2. dry with materialthe organic phase was dried over Na2SO4
  3. customevaporated
  4. customThe crude product was purified by column chromatography (eluent:DCM/MeOH/NH4OH 97:3:0.3)

Sources & evidence

ORD record
ord-dccd501a74a140608977988ed46d32f6
Source dataset
uspto-grants-2013_11
Patent number
US08592444B2

Reaction notes

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