1-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate → Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 1721704Notes

Reaction equation

HRID 1721704 reaction equation
[C:1]([N:11]1[CH2:19][C@H:17]([OH:18])[CH2:16][C@H:12]1[C:13](O)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]>C1COCC1>[CH2:4]([O:3][C:1]([N:11]1[CH2:19][C@H:17]([OH:18])[CH2:16][C@H:12]1[CH2:13][OH:14])=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 1

HCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Product 1

HCID 14994791Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylateYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cold solution of 4.76 g (18 mmoles) of CBZ hydroxyproline (Sigma Chemical Co.) in 20 mL of dry THF was added 45 mL of a 1M solution borane-THF complex in THF (Aldrich). After stirring under argon for 15 minutes at 0°-5° C., and 4.5 h at room temperature, the mixture was quenched with 50 mL of methanol. After 30 min, the solution was concentrated. The residual colorless syrup was purified by flash chromatography (3.5×23 cm silica) using a gradient of methanol in methylene chloride. The product eluted with 10% methanol. The fractions containing pure product were stripped of solvent to give 2.18 g (46% yield) of (1) as a colorless syrup.

Workup

  1. custom4.5 h at room temperature, the mixture was quenched with 50 mL of methanol
  2. waitAfter 30 min
  3. concentrationthe solution was concentrated
  4. customThe residual colorless syrup was purified by flash chromatography (3.5×23 cm silica)
  5. washThe product eluted with 10% methanol
  6. additionThe fractions containing pure product

Sources & evidence

ORD record
ord-04637e6141ee467caf26aab5fb417e8f
Source dataset
uspto-grants-1996_04
Patent number
US05512667

Reaction notes

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