Sodium sulfate decahydrate → 3-(Pyrrolidin-1-ylmethyl)thiomorpholine

HRID 2257293Notes

Reaction equation

HRID 2257293 reaction equation
[N:1]1([C:6]([CH:8]2[CH2:13][S:12][CH2:11][CH2:10][NH:9]2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[N:1]1([CH2:6][CH:8]2[CH2:13][S:12][CH2:11][CH2:10][NH:9]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 62649Sodium sulfate decahydrateHCID 166653Hydride2×HCID 3028194Lithium2×HCID 15730146HCID 15730146, compound

Product 1

HCID 157301473-(Pyrrolidin-1-ylmethyl)thiomorpholineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.6 g of 3-(pyrrolidine-1-carbonyl)thiomorpholine in 200 ml of tetrahydrofuran was added dropwise to a mixture of 1.0 g of lithium alminum hydride and 100 ml of tetrahydrofuran under ice-cooling and a stream of nitrogen. Excess lithium alminum hydride was decomposed using 15 g of sodium sulfate decahydrate. Celite filtration using methylene chloride was carried out. The solvent was concentrated under reduced pressure to yield 1.37 g (93%) of 3-(pyrrolidin-1-ylmethyl)thiomorpholine.

Workup

  1. temperaturecooling
  2. filtrationCelite filtration
  3. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b43c5d1ce94d4baf8b99392e59816402
Source dataset
uspto-grants-1997_08
Patent number
US05656758

Reaction notes

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