Ethyl Acetate → HCID 57959883, compound

HRID 1698493Notes

Reaction equation

HRID 1698493 reaction equation
[C:1]([S:5]([NH2:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH:8]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O.C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[C:1]([S:5](/[N:7]=[CH:8]\[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 3382465Tert-ButanesulfinamideHCID 10656219tert-Butyl 2-formylpiperidine-1-carboxylate

Product 1

HCID 57959883HCID 57959883, compound

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

tert-Butylsulphinamide (1.21 g, 10 mmol) was added to a stirred mixture of tert-butyl 2-formylpiperidine-1-carboxylate (1.64 g, 7.7 mmol) and titanium ethoxide (3.2 mL, 15.4 mmol) in THF (20 mL). The reaction mixture was stirred for 12 h at ambient temperature, poured into a bi-phasic mixture of brine (100 mL) and ethyl acetate (100 mL) and stirred for a further 30 min. The mixture was filtered through a pad of Celite and the phases were separated. The organic phase was dried (MgSO4) and concentrated to give the title product which was used without purification (2.77 g). 1H NMR (400 MHz, CDCl3): δ 7.93 (1H, dd, J=6.8, 2.1 Hz), 5.03 (1H, br), 4.00 (1H, br s), 2.76-3.03 (1H, br), 2.1 (1H, d, J=13 Hz), 1.87-1.55 (3H, m), 1.50-1.40 (9H, br), 1.36-1.13 (11H, m),

Workup

  1. stirringstirred for a further 30 min
  2. filtrationThe mixture was filtered through a pad of Celite
  3. customthe phases were separated
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-043293c42fdd421b9fc62426fff5b575
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

Loading…