Benzyl Bromide → HCID 86723936, compound

HRID 1475293Notes

Reaction equation

HRID 1475293 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].C(N(CC)CC)C.[C:14]([O:18][C:19]([N:21]1[CH2:26][C@H:25]([CH2:27][CH3:28])[N:24]([CH2:29][C:30]([OH:32])=[O:31])[CH2:23][C@H:22]1[CH3:33])=[O:20])([CH3:17])([CH3:16])[CH3:15].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C=O)C>[C:14]([O:18][C:19]([N:21]1[CH2:26][C@H:25]([CH2:27][CH3:28])[N:24]([CH2:29][C:30]([O:32][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:31])[CH2:23][C@H:22]1[CH3:33])=[O:20])([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 86723934HCID 86723934, compound

Product 1

HCID 86723936HCID 86723936, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Cs2CO3 (3.4 g, 10.5 mmol) was added to a solution of (2R,5S)-4-carboxymethyl-5-ethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester triethylamine salt (3.9 g, 9.6 mmol) in DMF (20 mL). After stirring for 2 h at room temperature, a solution of benzyl bromide (1.25 mL, 10.5 mmol) in DMF (10 mL) was added over 30 minutes. The reaction mixture was stirred overnight at room temperature and the resulting solid was filtered off and the filtrate was evaporated in vacuo. The residue was dissolved in EtOAc and washed with water. The organic phase was dried (MgSO4), filtered and concentrated and the residue was purified by SiO2 chromatography (EtOAc:Petrol 1:1) to give (2R,5S)-4-benzyloxycarbonylmethyl-5-ethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (2.8 g) as a pale yellow oil. 1H NMR (CDCl3): 7.45-7.29 (5H, m), 5.26-5.08 (2H, m), 4.27-4.08 (1H, m), 3.89 (1H, d), 3.52-3.22 (3H, m), 2.75 (1H, dd), 2.68-2.40 (2H, m), 1.47 (11H, d), 1.26 (3H, d), 0.90 (3H, t).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. filtrationthe resulting solid was filtered off
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue was purified by SiO2 chromatography (EtOAc:Petrol 1:1)

Sources & evidence

ORD record
ord-31ec806980164c2984346248169800be
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

Loading…