Sodium Sulfate → HCID 89543564, compound

HRID 922781Notes

Reaction equation

HRID 922781 reaction equation
[CH:1]1([CH:4]2[CH2:9][NH:8][C:7](=O)[CH2:6][S:5]2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH:1]1([CH:4]2[S:5][CH2:6][CH2:7][NH:8][CH2:9]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 89543728HCID 89543728, compound

Product 1

HCID 89543564HCID 89543564, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-cyclopropylthiomorpholin-3-one (4-13, 355 mg, 2.258 mmol) in THF (10 ml) was cooled to 0° C. To this was added 2M LAH (2.3 ml, 4.60 mmol) slowly. After the addition was complete the cooling bath was removed and the mixture allowed to warm to rt. After stirring overnight the mixture was cooled to 0° C. and slowly quenched with 2M NaOH until gas evolution had ceased and a fine white precipitate formed. Anhydrous Na2SO4 was added and the mixture stirred for 15 minutes. The slurry was filtered through a pad of Celite washing with THF and the filtrate concentrated to afford 2-cyclopropylthiomorpholine (4-14, 242 mg, 75%) as a pale yellow oil which was used in subsequent steps as is.

Workup

  1. additionAfter the addition
  2. customwas removed
  3. temperaturewas cooled to 0° C.
  4. customslowly quenched with 2M NaOH until gas evolution
  5. customa fine white precipitate formed
  6. stirringthe mixture stirred for 15 minutes
  7. filtrationThe slurry was filtered through a pad of Celite
  8. washwashing with THF
  9. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-06ed3f94c7d64b27827299239f0e3200
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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