Benzyl Bromide → HCID 10903207, compound

HRID 1527393Notes

Reaction equation

HRID 1527393 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[CH2:13])[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[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(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[CH2:13])[CH2:10][C@H:9]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 21727417(2S)-1-((tert-butoxy)carbonyl)-4-methylidenepyrrolidine-2-carboxylic acid

Product 1

HCID 10903207HCID 10903207, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid (4 g, 17.60 mmol) dissolved in DMF (100 mL) at 0° C. were added benzyl bromide (2.51 mL, 21.12 mmol) and cesium carbonate (6.31 g, 19.36 mmol). The solution was stirred 16 h at RT then was concentrated. Purification by flash column chromatography on silica gel (c-hexane/EtOAc 1:1). MS (UPLC/MS): 218 [MH−tBu]+, tR (HPLC conditions f): 2.44 min.

Workup

  1. concentrationthen was concentrated
  2. customPurification by flash column chromatography on silica gel (c-hexane/EtOAc 1:1)
  3. custom2.44 min.

Sources & evidence

ORD record
ord-c340c5ee52404487801fe71a31dbd4be
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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