HCID 178471800, compound → HCID 178471796, compound

HRID 409497Notes

Reaction equation

HRID 409497 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13](O)=[O:14])[CH2:9][CH2:8]1)=[O:5])[CH3:2]>C1COCC1>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][OH:14])[CH2:9][CH2:8]1)[CH3:2]

Participants

3

Reactant 1

HCID 178471800HCID 178471800, compound

Product 1

HCID 178471796HCID 178471796, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trans-4-ethoxycarbonylmethyl-cyclohexanecarboxylic acid (1 mmol; 214 mg) in THF (3 mL) is added 1.0 M THF solution of borane THF complex (2 mmol; 2 mL) at 0° C. under nitrogen. The solution is stirred for 1.5 hours at room temperature, quenched by dropwise addition of 1 mL of MeOH. The mixture after concentration is diluted with dichloromethane and saturated aqueous ammonium chloride solution. The product is extracted with 100 ml of dichloromethane. The organic layer after dried is separated, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (n-hexane/EtOAc) to give trans-(4-hydroxymethylcyclohexyl)-acetic acid ethyl ester (166 mg, 83%); ESI-MS m/z: 201 [M++1], Retention time 1.67 min (condition A).

Workup

  1. customquenched by dropwise addition of 1 mL of MeOH
  2. concentrationThe mixture after concentration
  3. additionis diluted with dichloromethane and saturated aqueous ammonium chloride solution
  4. extractionThe product is extracted with 100 ml of dichloromethane
  5. customThe organic layer after dried
  6. customis separated
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by column chromatography on silica gel (n-hexane/EtOAc)

Sources & evidence

ORD record
ord-5acc975b83c547b993ffd23a44d9cd4e
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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