Tert-Butanesulfinamide → HCID 87263096, compound

HRID 1665107Notes

Reaction equation

HRID 1665107 reaction equation
[CH3:1][C:2]1([CH3:20])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH:18]=O)=[CH:11][CH:10]=2)[CH2:4][O:3]1.[C:21]([S:25]([NH2:27])=[O:26])([CH3:24])([CH3:23])[CH3:22]>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH3:1][C:2]1([CH3:20])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17]/[CH:18]=[N:27]/[S:25]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:26])=[CH:11][CH:10]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 86641905HCID 86641905, compound

Product 1

HCID 87263096HCID 87263096, compound

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 4-[4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-butyraldehyde (4.28 g, 15.4 mmol) in THF (150 ml) is added tert-butyl sulfinamide (2.05 g, 16.9 mmol) followed by titanium ethoxide (6.5 ml, 30.8 mmol). The yellow solution formed is stirred at room temperature overnight. The solution is quenched with 1 N NaOH (200 ml) and EtOAc (100 ml) and stirred for 30 minutes at room temperature. The resultant mixture is filtered through Celite™ (filter material) and the organic phase is separated and dried (MgSO4). Concentration in vacuo gives 2-Methyl-propane-2-sulfinic acid [4-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-but-(E)-ylidene]-amide as a yellow oil; [M+H]+ 382.23

Workup

  1. customThe yellow solution formed
  2. customThe solution is quenched with 1 N NaOH (200 ml) and EtOAc (100 ml)
  3. stirringstirred for 30 minutes at room temperature
  4. filtrationThe resultant mixture is filtered through Celite™ (filter material)
  5. customthe organic phase is separated
  6. dry with materialdried (MgSO4)
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-3ae04c3697374e0193afe38ec680d7d6
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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