Methanol → [1-(2-Hydroxy-ethyl)-cyclohexyl]-acetic acid benzyl ester

HRID 455900Notes

Reaction equation

HRID 455900 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][C:12]1([CH2:18][C:19](O)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>O1CCCC1>[CH2:1]([O:8][C:9](=[O:10])[CH2:11][C:12]1([CH2:18][CH2:19][OH:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 14036669(1-Benzyloxycarbonylmethyl-cyclohexyl)-acetic acid

Product 1

HCID 66675168[1-(2-Hydroxy-ethyl)-cyclohexyl]-acetic acid benzyl esterYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (1-benzyloxycarbonylmethyl-cyclohexyl)-acetic acid (3.0 g, 10 mmol) in tetrahydrofuran (20 mL) was cooled to 0° C. and 1 M borane-THF complex in tetrahydrofuran (21 mL, 20 mmol) was added dropwise over 5 min. The reaction mixture was allowed to warm to room temperature, stirred for 1 h at room temperature. and cooled to 0° C. Methanol was added slowly to quench the reaction. The reaction mixture was warmed to room temperature, stirred for 30 min, and concentrated to dryness to provide the title compound (2.2 g).

Workup

  1. temperatureand cooled to 0° C
  2. customto quench
  3. customthe reaction
  4. temperatureThe reaction mixture was warmed to room temperature
  5. stirringstirred for 30 min
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d31d172f80714641911dca9dc151ffb0
Source dataset
uspto-grants-2013_07
Patent number
US08497287B2

Reaction notes

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