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

HRID 1879311Notes

Reaction equation

HRID 1879311 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-5fdd5eafbe444fc1aeef0dda365744ae
Source dataset
uspto-grants-2012_11
Patent number
US08314128B2

Reaction notes

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