HCID 66890305, compound → HCID 58104614, compound

HRID 1671373Notes

Reaction equation

HRID 1671373 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]([OH:16])[CH2:14][CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([OH:16])[CH2:14][CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 66890305HCID 66890305, compound

Product 1

HCID 58104614HCID 58104614, compound

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

(S)-3-(1-Hydroxypropyl)pyrrolidine-1-carboxylic acid t-butyl ester (1.5 g, 6.5 mmol) was purified by preparative HPLC. The residue was dissolved in 50% AcOH/H2O and the diastereomers were separated using a gradient of 10-50% AcOH/H2O (0.05% TFA) over 80 minutes on a 2″ column at 40 mL/min. The collected fractions were lyophilized to yield each diastereomer as an oil (565 mg, SS, 1st eluting peak; 565 mg, SR, 2nd eluting peak). Each diastereomer was dissolved in DCM (4 mL) and HCO3 resin (1 g @ 1.95 mmol/g) was added to recover residual TFA. The mixture was stirred for 1 hour. The product was filtered off and solvent was removed to yield the title compound.

Workup

  1. customthe diastereomers were separated
  2. customover 80 minutes
  3. customto yield each diastereomer
  4. washas an oil (565 mg, SS, 1st eluting peak; 565 mg, SR, 2nd eluting peak)
  5. dissolutionEach diastereomer was dissolved in DCM (4 mL)
  6. additionHCO3 resin (1 g @ 1.95 mmol/g) was added
  7. customto recover residual TFA
  8. filtrationThe product was filtered off
  9. customsolvent was removed

Sources & evidence

ORD record
ord-1d9fa2e3df6744c9af35c8390cab14f1
Source dataset
uspto-grants-2011_08
Patent number
US07994209B2

Reaction notes

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