Benzyl Bromide → benzyl (S)-1-tert-butoxycarbonylpyrrolidine-3-carboxylate

HRID 928055Notes

Reaction equation

HRID 928055 reaction equation
C1CCN2C(=NCCC2)CC1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20]([O:24][C:25]([N:27]1[CH2:31][CH2:30][C@H:29]([C:32]([OH:34])=[O:33])[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>C1(C)C=CC=CC=1>[C:20]([O:24][C:25]([N:27]1[CH2:31][CH2:30][C@H:29]([C:32]([O:34][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:33])[CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1512492(3S)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid

Product 1

HCID 59016658benzyl (S)-1-tert-butoxycarbonylpyrrolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

DBU (0.764 mL) was added to a mixture of benzyl bromide (0.61 mL), (S)-1-tert-butoxycarbonyl-pyrrolidine-3-carboxylic acid (1 g) in anhydrous toluene (10 mL) and the mixture was stirred at room temperature for 24 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-35% to give benzyl (S)-1-tert-butoxycarbonylpyrrolidine-3-carboxylate (0.859 g)

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-35%

Sources & evidence

ORD record
ord-68de794ff3c6415c8404db350a5cfa37
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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