3-Cyclopentyloxy-4-methoxybenzaldehyde oxime → 3-(3-cyclopentyloxy-4-methoxy-phenyl)-1-oxa-2,7-diaza-spiro[4.4]non-2-ene-7-carboxylic Acid Tert-butyl Ester

HRID 1169853Notes

Reaction equation

HRID 1169853 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=[CH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:14]1([O:19][C:20]2[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[CH:23]=[N:24][OH:25])[CH2:18][CH2:17][CH2:16][CH2:15]1.Cl[O-].[Na+]>ClCCl.C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]2([O:25][N:24]=[C:23]([C:22]3[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:20]([O:19][CH:14]4[CH2:18][CH2:17][CH2:16][CH2:15]4)[CH:21]=3)[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 28228453-Cyclopentyloxy-4-methoxybenzaldehyde oximeHCID 15297967tert-Butyl 3-methylidenepyrrolidine-1-carboxylateHCID 23665760Sodium Hypochlorite

Product 1

HCID 114641843-(3-cyclopentyloxy-4-methoxy-phenyl)-1-oxa-2,7-diaza-spiro[4.4]non-2-ene-7-carboxylic Acid Tert-butyl Ester

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The compound obtained from step c above (170 mg, 0.0010 mole) and 3-cyclopentyloxy-4-methoxy-benzaldehyde oxime (236 mg, 0.0010 mole) were taken in dichloromethane (20%) in chloroform followed by the addition of pyridine (2 drops). The reaction mixture was stirred at room temperature for 10 minutes followed by the addition of sodium hypochlorite (2 mL) dropwise. The resulting reaction mixture was stirred at room temperature for 4 hours. Tetrahydrofuran was evaporated under reduced pressure followed by diluting it with water. The compound was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The residue thus obtained was purified by column chromatography to furnish the title compound. Yield: 200 mg.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature for 4 hours
  3. customTetrahydrofuran was evaporated under reduced pressure
  4. additionby diluting it with water
  5. extractionThe compound was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a27f9915a491468d95a82572a8312fdf
Source dataset
uspto-grants-2010_11
Patent number
US07825147B2

Reaction notes

Loading…