Acetic Acid → 2-Hydroxymethylclavam

HRID 582479Notes

Reaction equation

HRID 582479 reaction equation
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].CC(O)=O.[Si]([O:30][CH2:31][C@@H:32]1[O:38][C@@H:37]2[N:34]([C:35](=[O:39])[CH2:36]2)[CH2:33]1)(C(C)(C)C)(C)C.CCCCCC.C(OCC)(=O)C>C1COCC1>[OH:30][CH2:31][C@@H:32]1[O:38][C@@H:37]2[N:34]([C:35](=[O:39])[CH2:36]2)[CH2:33]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 15102546HCID 15102546, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 30502592-HydroxymethylclavamYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution of 1N Bu4NF (2.71 ml, 2.71 mmole) containing AcOH (90 mg, 1.5 mmole) was added to a solution of ref. compound 1A (465 mg, 1.81 mmole) in THF (5 ml) at 0-5° C. The mixture was stirred at room temperature for 2 hrs, then poured into a silica gel column. The column was eluented with hexane-ethyl acetate (1:2) and 250 mg of title compound was obtained as an oil.

Workup

  1. additionwas added to a solution of ref
  2. customat 0-5° C
  3. additionpoured into a silica gel column

Sources & evidence

ORD record
ord-23421b9b9a494a268d94e2ff936d0ffc
Source dataset
uspto-grants-1999_07
Patent number
US05925633

Reaction notes

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