tert-Butylsulfinamide, (S)-(-)- → (NE,S)-2-methyl-N-(oxetan-3-ylmethylidene)propane-2-sulfinamide

HRID 246271Notes

Reaction equation

HRID 246271 reaction equation
[O:1]1[CH2:4][CH:3]([CH:5]=O)[CH2:2]1.[CH3:7][C:8]([S@@:11]([NH2:13])=[O:12])([CH3:10])[CH3:9]>ClCCl.S([O-])([O-])(=O)=O.[Cu+2]>[O:1]1[CH2:4][CH:3](/[CH:5]=[N:13]/[S@:11]([C:8]([CH3:10])([CH3:9])[CH3:7])=[O:12])[CH2:2]1

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 53346603Oxetane-3-carbaldehyde

Product 1

HCID 89421069(NE,S)-2-methyl-N-(oxetan-3-ylmethylidene)propane-2-sulfinamideYield 29%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

In a round-bottomed flask, oxetane-3-carbaldehyde (452 mg, 3.15 mmol) was dissolved in dichloromethane (18 ml) and (S)-2-methylpropane-2-sulfinamide (435 mg, 3.59 mmol) and anhydrous copper (II) sulfate (1.11 g, 6.93 mmol) were added. The reaction mixture was stirred at room temperature for 48 h then filtered through a glass microfiber filter, rinsing with dichloromethane. The filtrate was concentrated and the residue was chromatographed over silica gel with EtOAc/hexanes (gradient: 0-30% EtOAc) to afford 173 mg (29%) of (S)-2-methyl-propane-2-sulfinic acid 1-oxetan-3-yl-meth-(E)-ylideneamide as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.28 (d, J=4.9 Hz, 1H), 4.74-5.00 (m, 4H), 4.00-4.19 (m, 1H), 1.23 (s, 9H).

Workup

  1. filtrationthen filtered through a glass microfiber
  2. filtrationfilter
  3. washrinsing with dichloromethane
  4. concentrationThe filtrate was concentrated
  5. customthe residue was chromatographed over silica gel with EtOAc/hexanes (gradient: 0-30% EtOAc)

Sources & evidence

ORD record
ord-a9628c694983432e85624349a5bda2e0
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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