Calcium Chloride → HCID 68809401, compound

HRID 434297Notes

Reaction equation

HRID 434297 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=1)[CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Ca+2].[Cl-]>C(O)(=O)C.[Zn]>[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([C:16](=[O:24])[C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 5284359Calcium ChlorideHCID 68809762HCID 68809762, compound

Product 1

HCID 68809401HCID 68809401, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [(R)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-1-(4-nitro-benzyl)-ethyl]-carbamic acid tert-butyl ester (1.41 g, 2.90 mmol) in acetic acid (11 ml), cooled to 0° C., is added an aqueous solution of calcium chloride (4 ml, 0.47M) and zinc dust (3.9 g, 59.6 mmol). The reaction mixture is stirred at 0° C. for 35 minutes and then filtered through a celite plug. The filtrate is evaporated and the residue dissolved in water and extracted into dichloromethane. The dichloromethane is evaporated and the residue disolved in water and basified with aqueous sodium bicarbonate solution and extracted into dichloromethane. The dichloromethane is dried over magnesium sulphate and evaporated to afford {(R)-1-(4-amino-benzyl)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester, [MH]+456.5.

Workup

  1. filtrationfiltered through a celite plug
  2. customThe filtrate is evaporated
  3. dissolutionthe residue dissolved in water
  4. extractionextracted into dichloromethane
  5. customThe dichloromethane is evaporated
  6. extractionthe residue disolved in water and basified with aqueous sodium bicarbonate solution and extracted into dichloromethane
  7. dry with materialThe dichloromethane is dried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-34d2aee794934cc0bbdf4eae8df04697
Source dataset
uspto-grants-2003_12
Patent number
US06670379B2

Reaction notes

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