Benzyl Bromide → 862885-08-3

HRID 1970480Notes

Reaction equation

HRID 1970480 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[C:2]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:12]1)=[O:7])([CH3:1])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid

Product 1

HCID 12162212862885-08-3

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1.00 g Boc-1-pyrrolidine-3-carboxylic acid in 10 ml toluene were added 0.61 ml benzyl bromide and 0.76 ml DBU. After stirring for 12 h the reaction mixture was washed with water and the crude product obtained after evaporation of the solvent was purified by flash chromatography on silica using ethyl acetate/heptane 1:3 as eluent.

Workup

  1. washwas washed with water

Sources & evidence

ORD record
ord-5e090e01c4b44b3ba48ab3197402c077
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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