Potassium Hydroxide → HCID 90037501, compound

HRID 1055385Notes

Reaction equation

HRID 1055385 reaction equation
[OH-].[K+].[CH2:3]([N:10]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:11]([C:17]1([OH:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:12]([O:14]CC)=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.OS([O-])(=O)=O.[K+]>O.CO>[CH2:24]([N:10]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:11]([C:17]1([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[C:12]([OH:14])=[O:13])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 516920Potassium bisulfateHCID 90037499HCID 90037499, compound

Product 1

HCID 90037501HCID 90037501, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

KOH (1.44 g, 25.6 mmol, Eq: 6) in H2O (20 mL) was added to as solution of ethyl 2-(dibenzylamino)-2-(1-hydroxycyclohexyl)acetate (1.63 g, 4.27 mmol, Eq: 1.00) in MeOH (60 mL) and the mixture was heated to 60° C. After 18 h the reaction was cooled to RT and diluted with 100 mL H2O. The pH of the reaction was adjusted to about 4 using sat. KHSO4, and extracted with EtOAc. The combined extracts were washed with H2O, dried over Na2SO4 and concentrated the title compound as a white foam (1.44 g, 95%) which was used without purification. MS m/e 354.1 (MH+).

Workup

  1. temperatureAfter 18 h the reaction was cooled to RT
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated the title compound as a white foam (1.44 g, 95%) which
  6. customwas used without purification

Sources & evidence

ORD record
ord-81e2194010634f26ab99c6cefc1e0e08
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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