Water → HCID 54087103, compound

HRID 2289388Notes

Reaction equation

HRID 2289388 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C@H:8]([CH2:17][C@H:18]([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:9][C:10](OC(C)(C)C)=[O:11].O.[OH-].[Na+]>C1COCC1>[F:7][C@H:8]([CH2:17][C@H:18]([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:9][CH2:10][OH:11]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53854579HCID 53854579, compound

Product 1

HCID 54087103HCID 54087103, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
5 °C

Procedure

In a 100 ml flask were charged dried THF and 0.7 g of lithium aluminum hydride in a nitrogen stream, followed by cooling to 10° C. or less. A solution of 4.2 g of t-butyl (3R,5R)-3-fluoro-5-methylnonanoate obtained in Step 7 in 13 ml of dried THF was added thereto over 30 minutes, and the resulting mixture was allowed to react at 30 to 35° C. for 1.5 hours. After cooling to 5° C., a mixture of 0.7 ml of water and 2 ml of THF was added thereto over 30 minutes, and 1.5 ml of a 4% sodium hydroxide aqueous solution was then added, followed by stirring at that temperature for 1 hour. The by-produced salt was removed by filtration, and calcium carbonate was added to the filtrate to dry. The solvent was removed by distillation to obtain 2.9 g (96.5%) of a crude product.

Workup

  1. temperatureby cooling to 10° C. or less
  2. customto react at 30 to 35° C. for 1.5 hours
  3. additionwas added
  4. waitover 30 minutes
  5. customThe by-produced salt was removed by filtration, and calcium carbonate
  6. additionwas added to the filtrate
  7. customto dry
  8. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-8cb4f7fbb9564bff9ed41a9c647c78fd
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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