HCID 178457364, compound → HCID 12952545, compound

HRID 2417974Notes

Reaction equation

HRID 2417974 reaction equation
[CH2-]C(C)=O.[S:5]([N:9]([CH:15]([CH3:17])[CH3:16])[CH2:10][C@H:11]([OH:14])[CH2:12][OH:13])([CH3:8])(=[O:7])=[O:6]>CO.O>[S:5]([N:9]([CH:15]([CH3:17])[CH3:16])[CH2:10][C@H:11]([OH:14])[CH2:12][OH:13])([CH3:8])(=[O:6])=[O:7]

Participants

4

Reactant 1

HCID 178457364HCID 178457364, compound

Product 1

HCID 12952545HCID 12952545, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

200 ml of prewashed (water and methanol) Dowex 50W-8X ion exchange resin (H30 form) was added to a solution of 264 g crude (2S)-3-[N-mesyl-(1-methylethyl)amino]-1,2-propanediol acetonide in methanol (1 liter) and water (325 ml). The mixture was stirred under reflux for 90 minutes. The cooled mixture was filtered and the filtrate was concentrated in vacuo. The residue was evaporated several times from benzene-ethanol mixtures to remove the last traces of water. The resulting solid was triturated with 2.5 L ether to give 159.7 g of (2S)-3-[N-mesyl-(1-methylethyl)amino]-1,2-propanediol, mp 67°-70°. Concentration of the ether furnished an additional 27.7 g of (2S)-3-[N-mesyl-(1-methylethyl)amino]-1,2-propanediol, mp 62°-66°. Crystallization from ethyl acetate-hexane furnished the analytically pure material, mp 73°-74°; [α]D25 -15.94° (c, 1.0, H2O).

Workup

  1. temperatureunder reflux for 90 minutes
  2. filtrationThe cooled mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was evaporated several times from benzene-ethanol mixtures
  5. customto remove the last traces of water
  6. customThe resulting solid was triturated with 2.5 L ether

Sources & evidence

ORD record
ord-11cf725b3e2d49b0b498c2c3c95f9851
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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