Phosphoric Acid → (2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol phosphate

HRID 1992781Notes

Reaction equation

HRID 1992781 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][C@H:4]([CH3:17])[C@@:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)([OH:8])[CH2:6][CH3:7].[P:19](=O)([OH:22])([OH:21])[OH:20]>C(O)C>[P:19]([O:8][C@@:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)([CH2:6][CH3:7])[C@@H:4]([CH3:17])[CH2:3][N:2]([CH3:1])[CH3:18])([OH:22])([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 11708619(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol

Product 1

HCID 68535694(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol phosphateYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g (0.04 mol) of the enantiomeric pair (2R,3R)/(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol were dissolved in 40 ml of ethanol and treated with stirring with 3 g of 85 wt. % ortho-phosphoric acid. After 24 h, the crystals formed were filtered off under reduced pressure and dried for 24 h in a drying cabinet at 40° C. to a final pressure of 10 mbar. 2.2 g (16% of theoretical) of (2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol phosphate were obtained as colourless crystals with an enantiomeric purity of 85%.

Workup

  1. additiontreated
  2. customthe crystals formed
  3. filtrationwere filtered off under reduced pressure
  4. customdried for 24 h in a drying cabinet at 40° C. to a final pressure of 10 mbar

Sources & evidence

ORD record
ord-5519e187898546dca10d6c4e36fc840b
Source dataset
uspto-grants-2010_01
Patent number
US07649114B2

Reaction notes

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