Sodium Chloride → HCID 70214164, compound

HRID 380529Notes

Reaction equation

HRID 380529 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:10]([O:23]C(=O)CCl)[CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].[Na+].[Cl-]>CO>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:10]([OH:23])[CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 86757492HCID 86757492, compound

Product 1

HCID 70214164HCID 70214164, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.173 g (0.44 mmol) of 1-butyloxycarbonyl(cis)-3-(chloroacetoxy)-4-(3-phenylpropyl)piperidine and 0.30 g (2.2 mmol) of K2CO3 in 5 mL of methanol was stirred at rt for 24 h. To the reaction mixture was added 20 mL of sat'd NaCl solution and the mixture was extracted with ether. The combined organic fractions were dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 1:1) to give 1-butyloxycarbonyl (cis)-3-hydroxy-4-(3-phenylpropyl)piperidine. Removal of the BOC protecting group was achieved as described in Example 233, Step 6 to give the title compound.

Workup

  1. extractionthe mixture was extracted with ether
  2. dry with materialThe combined organic fractions were dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-937f732ca06b4cdfb9658198796db4f6
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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