2-(Dimethylamino)ethanol → HCID 59541938, compound

HRID 1893266Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11](=[O:14])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Into a solution of 4-(4-hydroxy-phenyl)cyclohexanone (as prepared in Example 40, Step E, 2.4 g, 12.6 mmol), N,N-dimethylethanolamine (Aldrich, 3.37 g, 37.8 mmol) and triphenylphosphine (Aldrich, 9.91 g, 37.8 mmol) in THF (100 mL) at 0° C. was added dropwise a solution of diisopropyl azodicarboxylate (7.44 mL, 37.8 mmol) in THF (15 mL) under Ar. The resulting solution was stirred at 0° C. for 1 h and at room temperature overnight. The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate concentrated in vacuo to give a colorless oil, which was purified on a silica gel column by a CombiFlash® system using hexanes and ethyl acetate as eluent (from pure hexanes to pure ethyl acetate) to afford the title compound as a white solid.

Workup

customThe solvent was removed
customthe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationthe filtrate concentrated in vacuo
customto give a colorless oil, which
customwas purified on a silica gel column by a CombiFlash® system

Sources & evidence

ORD record: ord-f90b02feb33f4d2ca049e5e5c91ca337
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513229B2

Reaction notes

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