Tetrabutylammonium Fluoride → (R)-Methyl 5-(3-(3-(hydroxymethyl)-1,1-dioxidoisothiazolidin-2-yl)-propyl)-thiophene-2-carboxylate

HRID 524363Notes

Reaction equation

HRID 524363 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:36][CH2:37][C@H:38]1[CH2:42][CH2:41][S:40](=[O:44])(=[O:43])[N:39]1[CH2:45][CH2:46][CH2:47][C:48]1[S:52][C:51]([C:53]([O:55][CH3:56])=[O:54])=[CH:50][CH:49]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.CCOC(C)=O>[OH:36][CH2:37][C@H:38]1[CH2:42][CH2:41][S:40](=[O:43])(=[O:44])[N:39]1[CH2:45][CH2:46][CH2:47][C:48]1[S:52][C:51]([C:53]([O:55][CH3:56])=[O:54])=[CH:50][CH:49]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735581HCID 131735581, compound

Product 1

HCID 118688790(R)-Methyl 5-(3-(3-(hydroxymethyl)-1,1-dioxidoisothiazolidin-2-yl)-propyl)-thiophene-2-carboxylateYield 73.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium fluoride (1.95 mL of a 1.0M solution in THF, 1.95 mmol) was added to a solution of the silyl ether 9 (751 mg, 1.29 mmol) in THF (3.0 mL). After stirring for 16 h the reaction was diluted with EtOAc and washed with water followed by brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex followed by 40% EtOAc/hex) afforded 317 mg (73%) of alcohol 10.

Workup

  1. washwashed with water
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex followed by 40% EtOAc/hex)

Sources & evidence

ORD record
ord-b03920a0709545f08aea8467b1d94392
Source dataset
uspto-grants-2016_05
Patent number
US09340534B2

Reaction notes

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