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

HRID 37027

Reaction equation

HRID 37027 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 min 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-673dcebd3c1f4bf982f5647338d23688
Source dataset
uspto-grants-1995_05
Patent number
US05419966

Linked notes

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