Methanol → HCID 22147672, compound

HRID 1823934Notes

Reaction equation

HRID 1823934 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17]1[O:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:20][N:21]=1)=O)C1C=CC=CC=1.C[Si](I)(C)C.CO>C(Cl)(Cl)Cl>[C:22]1([C:19]2[O:18][C:17]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][NH:11]3)=[N:21][CH:20]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 23570716HCID 23570716, compound

Product 1

HCID 22147672HCID 22147672, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 0.56 g (1.5 mmol) of 2-(5-Phenyl-oxazol-2-yl)-piperidine-1-carboxylic acid benzyl ester in 5 mL of chloroform, cooled in an ice bath under argon, was added 5 mL of trimethylsilyliodide. The mixture was allowed to slowly warm to room temperature and stir for five hours. To the reaction mixture was added 10 mL of methanol and the resulting mixture was allowed to stir at room temperature for 0.5 hour. The resulting mixture was partitioned between diethyl ether and 2N hydrochloric acid. The aqueous layer was separated, basified with 2N sodium hydroxide and extracted twice with diethyl ether. The combined ethyl ether extracts were dried over magnesium sulfate and concentrated to 0.20 g (0.88 mmol, 58% yield) of a yellow oil. The oil was 98% pure by LC analysis.

Workup

  1. stirringto stir at room temperature for 0.5 hour
  2. customThe resulting mixture was partitioned between diethyl ether and 2N hydrochloric acid
  3. customThe aqueous layer was separated
  4. extractionextracted twice with diethyl ether
  5. dry with materialThe combined ethyl ether extracts were dried over magnesium sulfate

Sources & evidence

ORD record
ord-0d54e9fc64ca4930830fc4eaa2a0f230
Source dataset
uspto-grants-2006_05
Patent number
US07041681B2

Reaction notes

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