Tert-Butanesulfinamide → Ethyl 6-((tert-butylsulfinyl)imino)hexanoate

HRID 594325Notes

Reaction equation

HRID 594325 reaction equation
O=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:12][C:13]([S:16]([NH2:18])=[O:17])([CH3:15])[CH3:14]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[C:13]([S:16]([N:18]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:17])([CH3:15])([CH3:14])[CH3:12]

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 11171124Ethyl 6-oxohexanoate

Product 1

HCID 86695621Ethyl 6-((tert-butylsulfinyl)imino)hexanoate

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A yellow solution of ethyl 6-oxohexanoate (44.80 mmol) in DCM (92 ml) was treated with 2-methylpropane-2-sulfinamide (5.431 g; 44.80 mmol) and with anh. CuSO4 (14.302 g; 89.61 mmol). The resulting beige heterogeneous mixture was further stirred at rt, under nitrogen, for 24 h. The resulting heterogeneous mixture was then filtered over a short pad of celite, and the separated solids were further washed with DCM. The obtained orange filtrate was concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded ethyl 6-((tert-butylsulfinyl)imino)hexanoate as a yellow/orange oil. LC-MS (conditions B): tR=0.81 min.; [M+H]+: 262.07 g/mol.

Workup

  1. filtrationThe resulting heterogeneous mixture was then filtered over a short pad of celite
  2. washthe separated solids were further washed with DCM
  3. concentrationThe obtained orange filtrate was concentrated to dryness under reduced pressure
  4. customPurification by FC (DCM/MeOH=25/1)

Sources & evidence

ORD record
ord-8f62a4ac96a54066ade31d30cf61ccf2
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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