Ammonium Chloride → HCID 53818593, compound

HRID 1378690Notes

Reaction equation

HRID 1378690 reaction equation
C(OC(C1CCNCC1)=O)C.C([O:14][C:15]([CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]3=[O:39])=[CH:25][C:24]=2[F:40])[CH2:19][CH2:18]1)=O)C.[Cl-].[Li+].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C.C1COCC1>[F:40][C:24]1[CH:25]=[C:26]([N:29]2[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]2=[O:39])[CH:27]=[CH:28][C:23]=1[N:20]1[CH2:21][CH2:22][CH:17]([CH2:15][OH:14])[CH2:18][CH2:19]1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 70770Ethyl 4-piperidinecarboxylateHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 53764065HCID 53764065, compound

Product 1

HCID 53818593HCID 53818593, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using a commercially available piperidine-4-carboxylic acid ethyl ester, (S)-1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperidine-4-carboxylic acid ethyl ester (Compound No. 1) was synthesized by the same method as in Example 1. To a THF solution (6.6 ml) of this compound (661 mg), lithium chloride (275 mg), sodium borohydride (245 mg) and ethanol (4.5 ml) were added successively and the mixture was stirred at room temperature for 14 h. A saturated aqueous ammonium chloride solution was added to the reaction solution and the reaction mixture was extracted with methylene chloride; the organic layer was washed with water and brine, dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (solvent: chloroform/methanol=25/1-15/1) to afford the title compound (402 mg) in a yield of 68%.

Workup

  1. customwas synthesized by the same method as in Example 1
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (solvent: chloroform/methanol=25/1-15/1)

Sources & evidence

ORD record
ord-c01f0418bd384f3caa99a80f5d70d35a
Source dataset
uspto-grants-1997_09
Patent number
US05668286

Reaction notes

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