4-Bromobenzyl bromide → HCID 11361507, compound

HRID 2182587Notes

Reaction equation

HRID 2182587 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Br:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:16])[C@:4]1([CH2:32][C:31]2[CH:34]=[CH:35][C:28]([Br:27])=[CH:29][CH:30]=2)[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10]

Participants

6

Reactant 3

HCID 685274-Bromobenzyl bromideHCID 1277666Boc-L-Pro-OmeHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 11361507HCID 11361507, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)proline methyl ester (1.30 g) in THF (20 mL) at −78° C. was added a solution of KHMDS (1.25 g) in THF (20 mL). After 45 minutes, a solution of 4-bromobenzyl bromide (1.59 g) in THF (20 mL) was added at −78° C. The reaction mixture was warmed to room temperature over 3 hours and stirred for an additional 3 hours. The mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography (silica gel; EtOAc/hexane 1:2) afforded N-(tert-butoxycarbonyl)-2-(4-bromobenzyl)proline methyl ester (0.474 g). MS (m/z) 398 (MH+).

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (silica gel; EtOAc/hexane 1:2)

Sources & evidence

ORD record
ord-ff609f531819485f866ead43b3d8d03e
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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