Potassium bisulfate → (S)-tert-butyl 1-oxohexan-2-ylcarbamate

HRID 342129Notes

Reaction equation

HRID 342129 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CON(C)[C:10](=[O:24])[C@@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:13][CH2:14][CH3:15].S([O-])(O)(=O)=O.[K+]>CCOCC.O>[C:20]([O:19][C:17]([NH:16][C@@H:11]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:10]=[O:24])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 10061913tert-butyl (1S)-1-{[methoxy(methyl)amino]carbonyl}pentylcarbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10420833(S)-tert-butyl 1-oxohexan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-45 °C

Procedure

A mechanically stirred suspension of lithium aluminum hydride (5.00 g, 0.131 mol) in ether (250 mL) was cooled to -45° C. under nitrogen. A solution of the product from Step A (28.3 g, 0.103 mol) in ether (125 mL) was added, maintaining the temperature below -35° C. When the addition was complete, the reaction was warmed to 5° C., then recooled to -45° C. A solution of potassium hydrogen sulfate (27.3 g, 0.200 mol) in water was slowly added, maintaining the temperature below -5° C. After quenching, the reaction was stirred at room temperature for 1 h. The mixture was filtered through Celite, the ether evaporated, and the remainder partitioned between ethyl acetate and 2% potassium hydrogen sulfate. After washing with saturated brine, drying over magnesium sulfate and solvent removal, the title compound was obtained.

Workup

  1. temperaturemaintaining the temperature below -35° C
  2. additionWhen the addition
  3. temperaturethe reaction was warmed to 5° C.
  4. customrecooled to -45° C
  5. temperaturemaintaining the temperature below -5° C
  6. customAfter quenching
  7. filtrationThe mixture was filtered through Celite
  8. customthe ether evaporated
  9. customthe remainder partitioned between ethyl acetate and 2% potassium hydrogen sulfate
  10. washAfter washing with saturated brine
  11. dry with materialdrying over magnesium sulfate and solvent removal

Sources & evidence

ORD record
ord-7a4916dbb0304362a152e1bfb89be82c
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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