1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 178451169, compound

HRID 1755032Notes

Reaction equation

HRID 1755032 reaction equation
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[OH:15][C@H:16]1[CH2:21][CH2:20][C@H:19](C(O)=O)[CH2:18][CH2:17]1>C1(C)C=CC=CC=1.CCOCC>[C:11]([O:10][C:6]([C@H:19]1[CH2:20][CH2:21][C@H:16]([OH:15])[CH2:17][CH2:18]1)=[O:5])([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 178525780HCID 178525780, compound

Product 1

HCID 178451169HCID 178451169, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

N,N-Dimethylformamide di-tert-butyl acetal (7.4 ml, 31 mmol) was added to a solution of trans-4-hydroxy-cyclohexanecarboxylic acid (1.484 g, 10.29 mmol) in toluene (8.5 ml), and the mixture was stirred at 80° C. for 25 hours. The reaction mixture was diluted with ether, and the organic layer was sequentially washed with water, an aqueous sodium bicarbonate solution and saturated brine, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give trans-4-hydroxy-cyclohexanecarboxylic acid tert-butyl ester as a colorless solid (838 m, 41%).

Workup

  1. washthe organic layer was sequentially washed with water
  2. dry with materialan aqueous sodium bicarbonate solution and saturated brine, dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a509a09ef5fd49638aeb651ff9539e3d
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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