Sulfuric Acid → HCID 90431900, compound

HRID 929433Notes

Reaction equation

HRID 929433 reaction equation
[CH3:1][C@:2]1([CH2:13][CH:14]=[O:15])[CH2:4][C@H:3]1[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].COC1CCCC1.[BH4-].[Na+].S(=O)(=O)(O)O>CO>[CH3:1][C@:2]1([CH2:13][CH2:14][OH:15])[CH2:4][C@H:3]1[CH:5]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:6]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 138539Cyclopentyl methyl etherHCID 4311764Sodium borohydrideHCID 90431831HCID 90431831, compound

Product 1

HCID 90431900HCID 90431900, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

under a nitrogen atmosphere, 2-[(1R*,2S*)-1-methyl-2-(1-phenylethyl)cyclopropyl]acetaldehyde (a diastereomer mixture with a component ratio of 1:2, 0.20 g, 0.99 mmol), cyclopentyl methyl ether (4 ml), and sodium borohydride (0.05 g, 1.3 mmol) were placed into a 30-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and methanol (0.05 g) was added with stirring at 20° C., followed by stirring at the same temperature for 60 minutes. Next, a 5% aqueous sulfuric acid solution (1.3 g) was added. After stirring for 10 minutes, the aqueous layer was separated, and the organic layer was washed twice with water (2 ml). The solvent was recovered under reduced pressure to obtain a condensed residue. This residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:2) to obtain 2-[(1R*,2S*)-1-methyl-2-(1-phenylethyl)cyclopropyl]ethanol (a diastereomer mixture with a component ratio of 1:2, 0.19 g, 0.93 mmol, 94% yield).

Workup

  1. customequipped with a stirring apparatus, a dropping funnel
  2. stirringby stirring at the same temperature for 60 minutes
  3. stirringAfter stirring for 10 minutes
  4. customthe aqueous layer was separated
  5. washthe organic layer was washed twice with water (2 ml)
  6. customThe solvent was recovered under reduced pressure
  7. customto obtain a condensed residue
  8. customThis residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-9c40423f31fa4f63b42c515075edaba1
Source dataset
uspto-grants-2016_03
Patent number
US09296675B2

Reaction notes

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