tert-Butylsulfinamide, (R)-(+)- → HCID 12995921, compound

HRID 1011606Notes

Reaction equation

HRID 1011606 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[CH2:8]1[CH:10]([CH:11](O)C#N)[CH2:9]1>C1COCC1.[Cl-].[Na+].O>[CH:10]1(/[CH:11]=[N:7]/[S@@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 113893592-Cyclopropyl-2-hydroxyacetonitrile

Product 1

HCID 12995921HCID 12995921, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(R)-2-Methylpropane-2-sulfinamide (25) (8.63 g, 71.3 mmol) and Ti(OEt)4 (30 mL, 142.6 mmol) were added to a solution of cyclopropylcarboxaldehyde (24) (5 g, 71.3 mmol) in THF (142 mL). The reaction mixture was stirred at rt for 17 h after which brine (142 mL) was added and the resulting suspension was filtered through a pad of Celite. The filtrate was extracted with EtOAc (200 mL) and the organic phase was dried (Na2SO4), filtered and concentrated under vacuum to give 12.7 g (quant) of (R,E)-N-(cyclopropylmethylene)-2-methylpropane-2-sulfinamide (26). Retention time (min)=1.459 method [1], MS (m/z) 174.1 (M+H)+.

Workup

  1. additionwas added
  2. filtrationthe resulting suspension was filtered through a pad of Celite
  3. extractionThe filtrate was extracted with EtOAc (200 mL)
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a271779ef3e541a2ac9366765d0a7c24
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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