Ammonium Chloride → HCID 11099734, compound

HRID 1620449Notes

Reaction equation

HRID 1620449 reaction equation
[O:1]=[C:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[C@H:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4][CH2:3]1.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[OH:1][C@@H:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[C@H:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 11045869HCID 11045869, compound

Product 1

HCID 11099734HCID 11099734, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 14.55 g (43.66 mmol) of (S)-1-benzyl 2-tertbutyl 5-oxopiperidine-1,2-dicarboxylate in ethanol (437 mL) was ice-cooled, and 1.65 g (43.62 mmol) of sodium borohydride was added, followed by allowing to react under ice cooling for 20 minutes. Saturated aqueous ammonium chloride solution was added dropwise to the reaction mixture until effervescence was quenched, and the generated salt was dissolved with the addition of water. The organic solvent of the mixture was distilled off under reduced pressure, and the aqueous layer of the residue was extracted with ethyl acetate. The organic layer was washed with saturated brine, followed by drying over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was applied to silica gel column chromatography (hexane/ethyl acetate=3/1→2/1) to afford 13.35 g of the title compound as a colorless oil (yield 91%). Enantiomeric excess: 98.8% ee (CHIRALPAK AD-H, 4.6×150 mm, UV 210 nm, hexane/ethanol=4/1, flow rate 1 mL/min., retention time 9.1 min.).

Workup

  1. temperaturecooled
  2. customto react under ice cooling for 20 minutes
  3. customwas quenched
  4. dissolutionthe generated salt was dissolved with the addition of water
  5. distillationThe organic solvent of the mixture was distilled off under reduced pressure
  6. extractionthe aqueous layer of the residue was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialby drying over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0d96e291543d4f0688eb2c80197c9342
Source dataset
uspto-grants-2014_07
Patent number
US08772490B2

Reaction notes

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