Tetrabutylammonium Fluoride → HCID 86658148, compound

HRID 454987Notes

Reaction equation

HRID 454987 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]([NH:16][C:17]([C@H:19]2[CH2:21][C@@H:20]2[C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:14][OH:15])=[C:9]([O:27][CH3:28])[CH:8]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:15][CH2:14][C@H:13]([NH:16][C:17]([C@H:19]1[CH2:21][C@@H:20]1[C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[C:10]1[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][C:9]=1[O:27][CH3:28]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67431353HCID 67431353, compound

Product 1

HCID 86658148HCID 86658148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the (1S,2S)-2-Thiophen-2-yl-cyclopropanecarboxylic acid {(R)-1-[4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-phenyl]-2-hydroxy-ethyl}-amide (393.4 mg, 0.88 mmol) dissolved in 20 ml THF at 0° C., was added 1.32 ml TBAF (1.0 M solution, 1.32 mmol). The ice bath was remove and stirred for 2 hr at rt. It was diluted with ether and quenched with aq. NH4Cl. The organic layer was washed with water and brine, and then dried over MgSO4. It was concentrated and purified on flash column (6% MeOH in DCM) to obtain the titled compound (used directly for next reaction).

Workup

  1. customThe ice bath was remove
  2. additionIt was diluted with ether
  3. customquenched with aq. NH4Cl
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationIt was concentrated
  7. custompurified on flash column (6% MeOH in DCM)

Sources & evidence

ORD record
ord-392ebbcaba0243e5936bc1b3574bb86c
Source dataset
uspto-grants-2013_07
Patent number
US08497271B2

Reaction notes

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