Benzyl Bromide → (S)-3-((S)-2-benzyloxy-1-hydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester

HRID 1254981Notes

Reaction equation

HRID 1254981 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([C@H:13]([OH:16])[CH2:14][OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl.[Ag]=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([C@H:13]([OH:16])[CH2:14][O:15][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 66857637(S)-3-((S)-1,2-dihydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 66859062(S)-3-((S)-2-benzyloxy-1-hydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl esterYield 39.6%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-((S)-1,2-dihydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester (294.0 mg, 1.3 mmol) in DCM (6.3 mL) at room temperature, was added benzyl bromide (181.4 μL, 1525 μmol) followed by silver(II) oxide (472.4 mg, 3.8 mmol). The resulting mixture was stirred overnight. The mixture was filtered and the filtrate was subjected to same amount of silver (II) oxide and benzyl bromide and stirred overnight. The mixture was concentrated and the residue was purified by flash chromatography (12 g silica gel, 0-50% EtOAc/Hexanes). Desired fractions were combined and concentrated to yield the title compound as a colorless oil (165.6 mg).

Workup

  1. filtrationThe mixture was filtered
  2. stirringstirred overnight
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by flash chromatography (12 g silica gel, 0-50% EtOAc/Hexanes)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3bdd4395f77140c49d765b6ad1e37988
Source dataset
uspto-grants-2013_06
Patent number
US08455665B2

Reaction notes

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