Ethanolamine → HCID 178455319, compound

HRID 1500637Notes

Reaction equation

HRID 1500637 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:27]([CH2:29][NH2:30])[OH:28]>C(#N)C.C(Cl)Cl>[Si:1]([O:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][NH:30][CH2:29][CH2:27][OH:28])[CH2:13][CH2:14]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 178427758HCID 178427758, compound

Product 1

HCID 178455319HCID 178455319, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of toluene-4-sulfonic acid trans-4-(tert-butyldimethylsilanyloxy)-cyclohexylmethyl ester (600 mg, 1.50 mmol) in acetonitrile (15 mL) was added ethanolamine (2.0 mL, 25 eq). The solution was heated to 50° C. overnight. The reaction was diluted with DCM (200 mL), washed with saturated aqueous sodium bicarbonate and brine, and dried over potassium carbonate. Solvent was removed to give crude title intermediate (0.44 g) as a yellow oil. (m/z): [M+H]+ calcd for C15H33NSiO2, 288.3. found 288.2.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over potassium carbonate
  3. customSolvent was removed

Sources & evidence

ORD record
ord-318d3ac2abe447f99180c8c51cf41eb7
Source dataset
uspto-grants-2015_12
Patent number
US09206172B2

Reaction notes

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