HCID 43581737, compound → (S)-2-(1,1-Dioxo-llambda*6*-thiomorpholin-4-yl)-1-methyl-ethylamine

HRID 1888909Notes

Reaction equation

HRID 1888909 reaction equation
[NH2:1][CH:2]([CH3:13])[C:3]([N:5]1[CH2:10][CH2:9][S:8](=[O:12])(=[O:11])[CH2:7][CH2:6]1)=O>C1COCC1>[O:12]=[S:8]1(=[O:11])[CH2:9][CH2:10][N:5]([CH2:3][C@@H:2]([NH2:1])[CH3:13])[CH2:6][CH2:7]1

Participants

3

Reactant 1

HCID 43581737HCID 43581737, compound

Product 1

HCID 93184900(S)-2-(1,1-Dioxo-llambda*6*-thiomorpholin-4-yl)-1-methyl-ethylamineYield 128.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-Amino-1-(1,1-dioxo-1lambda*6*-thiomorpholin-4-yl)-propan-1-one (6.0 g, 18.2 mmol) and BH3 (1 M in THF, 110 mL) was heated to reflux for 48 h, then cooled to room temperature and quenched by MeOH. The volatile was removed under vacuum. 2 N HCl (100 mL) was added to the residue and heated to reflux for 18 h. Solvent was removed under vacuum to give (S)-2-(1,1-Dioxo-1lambda*6*-thiomorpholin-4-yl)-1-methyl-ethylamine (4.5 g) as white solid, yield 90%. MS (M+H)=193.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. customquenched by MeOH
  4. customThe volatile was removed under vacuum
  5. addition2 N HCl (100 mL) was added to the residue
  6. temperatureheated
  7. temperatureto reflux for 18 h
  8. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-e51b9eb882b9443e843a3d3545443cdd
Source dataset
uspto-grants-2013_08
Patent number
US08501933B2

Reaction notes

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