Benzyl Alcohol → HCID 67032998, compound

HRID 2167896Notes

Reaction equation

HRID 2167896 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:21]([O:25][C:26](=[O:42])[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][S:32][CH:31]([C:35]2[CH:40]=[CH:39][C:38](I)=[CH:37][CH:36]=2)[CH2:30]1)([CH3:24])([CH3:23])[CH3:22].[CH2:43]([OH:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1(C)C=CC=CC=1.[Cu]I.O.CCOC(C)=O>[C:21]([O:25][C:26](=[O:42])[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][S:32][CH:31]([C:35]2[CH:40]=[CH:39][C:38]([O:50][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:37][CH:36]=2)[CH2:30]1)([CH3:24])([CH3:23])[CH3:22]

Participants

9

Reactant 4

HCID 244Benzyl AlcoholHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 66654135HCID 66654135, compound

Product 1

HCID 67032998HCID 67032998, compoundYield 88.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(All solutions were degassed) To a suspension of 1,10-phenanthroline (183.0 mg; 1.02 mmol) in toluene (15 mL) was added CuI (96.7 mg; 0.51 mmol), Cs2CO3 (3.31 g; 10.15 mmol), and a solution of 3-[2-(4-iodo-phenyl)-thiomorpholin-4-yl]-propionic acid tert-butyl ester (2.20 g; 5.08 mmol) and benzyl alcohol (1.05 mL; 10.15 mmol) in toluene (20 mL). The resulting mixture was heated for three days at 100° C. After cooling to RT EtOAc and water were added. The layers were separated and the organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, EtOAc/CH2Cl2 1:6) to afford 3-[2-(4-benzyloxy-phenyl)-thiomorpholin-4-yl]-propionic acid tert-butyl ester (1.85 g).

Workup

  1. custom(All solutions were degassed)
  2. additionwere added
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2, EtOAc/CH2Cl2 1:6)

Sources & evidence

ORD record
ord-d791de5237c94548a7a9735a221b6996
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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