Tetrabutylammonium Fluoride → tert-Butyl (2R,5R)-2-ethynyl-5-(hydroxymethyl)morpholine-4-carboxylate

HRID 629749Notes

Reaction equation

HRID 629749 reaction equation
[C:1]([C@H:3]1[O:8][CH2:7][C@H:6]([CH2:9][O:10][Si](C(C)(C)C)(C)C)[N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1)#[CH:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[C:1]([C@H:3]1[O:8][CH2:7][C@@H:6]([CH2:9][OH:10])[N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1)#[CH:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735383tert-butyl (2R,5R)-2-ethynyl-5-(tert-butyldimethylsilyloxy-methyl)morpholine-4-carboxylate

Product 1

HCID 86726348tert-Butyl (2R,5R)-2-ethynyl-5-(hydroxymethyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (2R,5R)-2-ethynyl-5-(tert-butyldimethylsilyloxy-methyl)morpholine-4-carboxylate (Example 79, step 4) (2.0 g, 5.7 mmol) in 20 mL of THF was added tetrabutylammonium fluoride (1.0 M in THF, 15 mL, 15 mmol). The solution was stirred at ambient temperature for 1 h and then diluted with EtOAc, washed with aqueous NH4Cl, and brine. The solution was dried (MgSO4), filtered, and the solvent was removed in vacuo. The residue was chromatographed on an 80 g SiO2 column using a gradient elution of 0-10% MeOH in CHCl3 to give the product as an oil.

Workup

  1. washwashed with aqueous NH4Cl, and brine
  2. dry with materialThe solution was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customThe residue was chromatographed on an 80 g SiO2 column
  6. washa gradient elution of 0-10% MeOH in CHCl3

Sources & evidence

ORD record
ord-2bbd49a0cf464146a845f161a1e38fa9
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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