Benzyl Bromide → HCID 15030796, compound

HRID 1614046Notes

Reaction equation

HRID 1614046 reaction equation
[C:1]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](=[O:27])[CH2:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])[CH:12]1[C:28]([OH:30])=[O:29])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1(NC2CCCCC2)CCCCC1>CN(C)C=O>[C:1]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](=[O:27])[CH2:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])[CH:12]1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 7582DicyclohexylamineHCID 19370159HCID 19370159, compound

Product 1

HCID 15030796HCID 15030796, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve N-carbobenzoxy-3[(diethoxyphosphinyl)acetyl]-piperidine-2-carboxylic acid (36.4 mmol) in dimethylformamide (200 mL) and place under a nitrogen atmosphere. Add benzyl bromide (10.5 mL), 81 mmol) and dicyclohexyl amine (16.2 mL, 89 mmol) and heat to 65° C. Allow to cool slowly to room temperature and filter. Pour the filtrate into water (11/2 L) and extract with ethyl acetate (2×500 mL). Combine the organic phases and dry (MgSO4). Evaporate the solvent in vacuo to give a brown oil. Purify by flash chromatography (ethyl acetate) to give the title compound as a yellow oil (3.6 g, 19%).

Workup

  1. filtrationfilter
  2. additionPour the filtrate into water (11/2 L)
  3. extractionextract with ethyl acetate (2×500 mL)
  4. dry with materialCombine the organic phases and dry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. customto give a brown oil
  7. customPurify by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-7e1cea58b8044a6eac27761b263d5376
Source dataset
uspto-grants-1993_03
Patent number
US05194430

Reaction notes

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