HCID 67301835, compound → HCID 67302146, compound

HRID 1015358Notes

Reaction equation

HRID 1015358 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12](O)=[O:13])[CH2:8][CH2:7]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][CH:6]1[CH2:7][CH2:8][CH:9]([CH2:12][OH:13])[CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 67301835HCID 67301835, compound

Product 1

HCID 67302146HCID 67302146, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(3-Chlorobenzyl)cyclohexanecarboxylic acid (550 mg; 2.2 mmol) was cooled to 0° C. in 5 mL of anhydrous tetrahydrofuran under nitrogen flow, and BH3 THF was added over 5 minutes. Mixture was warmed to room temperature. After 3.5 hours, mixture was cooled to 0° C. and quenched with slow additions of sat. NH4Cl. Mixture was stirred for 20 minutes and water was added to dissolve precipitates. Mixture was extracted 3×20 mL with ethyl acetate, and combined organics were washed with brine and dried over MgSO4. Material was purified via flash chromatography using 1-5% methanol in dichloromethane gradient to obtained 173 mgs of title compound. (33% yield)

Workup

  1. additionwas added over 5 minutes
  2. temperaturemixture was cooled to 0° C.
  3. customquenched with slow additions of sat. NH4Cl
  4. additionwater was added
  5. dissolutionto dissolve
  6. customprecipitates
  7. extractionMixture was extracted 3×20 mL with ethyl acetate
  8. washcombined organics were washed with brine
  9. dry with materialdried over MgSO4
  10. customMaterial was purified via flash chromatography

Sources & evidence

ORD record
ord-01a53e1ac21c4082bb66cf9da203cd24
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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