Ethyl Acetate → HCID 178472366, compound

HRID 413263Notes

Reaction equation

HRID 413263 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[O:7]2)[CH2:3][CH2:2]1.[CH2:16]([O:18][C:19]([C@H:21]1[CH2:26][CH2:25][C@H:24]([CH2:27][NH2:28])[CH2:23][CH2:22]1)=[O:20])[CH3:17].C[CH2:30][O:31]C(C)=O>>[CH2:16]([O:18][C:19]([C@H:21]1[CH2:26][CH2:25][C@H:24]([CH2:27][NH:28][C:30]([N:1]2[CH2:6][CH2:5][C:4]3([C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8](=[O:15])[O:7]3)[CH2:3][CH2:2]2)=[O:31])[CH2:23][CH2:22]1)=[O:20])[CH3:17]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-oneHCID 178472363HCID 178472363, compound

Product 1

HCID 178472366HCID 178472366, compound

Conditions

Temperature
60 °C

Procedure

Add spiro[isobenzofuran-1,4′-piperidin]-3-one (100 mg, 0.49 mmol) to 1 mL of a ˜0.2 M stock solution of 1′-(trans-4-ethoxycarbonyl-cyclohexylmethyl) carbamoyl chloride (prepared from trans-4-aminomethyl-cyclohexanecarboxylic acid ethyl ester using the same procedure given in Example 15 step A) and heat to 60° C. for 16 hours. Cool the solution, dilute with EtOAc and wash with brine. Dry the solution (Na2SO4) and concentrate under reduced pressure. Purify the crude product using preparative plate chromatography and triturate the resulting material with ether to obtain 1′-(trans-4-ethoxycarbonyl-cyclohexylmethyl)carbamoyl-spiro[isobenzofuran-1,4′piperidin]-3-one as a white solid.

Workup

  1. temperatureCool the solution
  2. washwash with brine
  3. dry with materialDry the solution (Na2SO4)
  4. concentrationconcentrate under reduced pressure
  5. customPurify the crude product
  6. customtriturate the resulting material with ether

Sources & evidence

ORD record
ord-59d318061950443797f07473de9d4c43
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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