Acetic Acid → HCID 59949122, compound

HRID 2387759Notes

Reaction equation

HRID 2387759 reaction equation
[OH:1][C@@H:2]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].O.C(O)(=O)C>C(O)C.[Rh]>[CH:12]1([CH2:11][C@H:2]([OH:1])[C:3]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)=[O:4])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 15172765HCID 15172765, compound

Product 1

HCID 59949122HCID 59949122, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2 (20.5 g, 87.1 mmol) in a mixture of ethanol (80 mL), water (10 mL) and acetic acid (10 mL) is charged to a Parr bomb and treated with 2 g of 10% Rh/C. The bomb is sealed, evacuated and pressurized to 1000 psi with hydrogen. The reaction is then heated to 50° C. with stirring overnight. After cooling to room temperature and relieving the pressure, the bomb is evacuated and back filled with nitrogen twice. The reaction mixture is filtered through a pad of celite and the solvent is removed to afford 18.6 g (88.5%) of (S)-3-cyclohexyl-2-hydroxy-1-morpholin-4-yl-propan-1-one (3) as an oil; HPLC-MS calculated for C13H23NO3 (M+H+) 242.2, found 242.4.

Workup

  1. additionis charged to a Parr bomb
  2. customThe bomb is sealed
  3. customevacuated
  4. temperatureAfter cooling to room temperature
  5. customthe bomb is evacuated
  6. additionback filled with nitrogen twice
  7. filtrationThe reaction mixture is filtered through a pad of celite
  8. customthe solvent is removed

Sources & evidence

ORD record
ord-8f81f01696cb41df9ca3698ebf297627
Source dataset
uspto-grants-2012_09
Patent number
US08268996B2

Reaction notes

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