Tert-Butanesulfinamide → 1-O-tert-butyl 4-O-methyl 4-[(2E)-2-tert-butylsulfinyliminoethyl]piperidine-1,4-dicarboxylate

HRID 1442904Notes

Reaction equation

HRID 1442904 reaction equation
O=[CH:2][CH2:3][C:4]1([C:17]([O:19][CH3:20])=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH3:21][C:22]([S:25]([NH2:27])=[O:26])([CH3:24])[CH3:23]>ClC(Cl)C.S([O-])([O-])(=O)=O.[Cu+2]>[C:22]([S:25](/[N:27]=[CH:2]/[CH2:3][C:4]1([C:17]([O:19][CH3:20])=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)=[O:26])([CH3:24])([CH3:23])[CH3:21]

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 589286301-Tert-butyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

Product 1

HCID 595551491-O-tert-butyl 4-O-methyl 4-[(2E)-2-tert-butylsulfinyliminoethyl]piperidine-1,4-dicarboxylateYield 80.4%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 1-tert-butyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate (822 mg, 2.88 mmol), copper(II) sulfate (1.38 g, 8.64 mmol) and 2-methyl-2-propanesulfinamide (354 mg, 3.17 mmol) in dichloroethane (15 mL) was heated at 65° C. for 24 h. The reaction was cooled, filtered and concentrated. The residue was partitioned between saturated aqueous NaHCO3 and dichloromethane, separated, the organic layer dried over MgSO4, and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of 0 to 7% methanol:dichloromethane to give the title compound (0.9 g). MS: m/z=389.2 (M+1).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was partitioned between saturated aqueous NaHCO3 and dichloromethane
  5. customseparated
  6. dry with materialthe organic layer dried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of 0 to 7% methanol

Sources & evidence

ORD record
ord-05a66c7620304b8990f28d551aea96c9
Source dataset
uspto-grants-2010_02
Patent number
US07659264B2

Reaction notes

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