Tetrabutylammonium Fluoride → (S)-3-((S)-1-(4-ethynylphenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

HRID 333910Notes

Reaction equation

HRID 333910 reaction equation
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].[OH:19][C:20]([CH3:50])([CH3:49])[CH2:21][C@@:22]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:27][C:26](=[O:28])[N:25]([C@H:29]([C:31]2[CH:36]=[CH:35][C:34]([C:37]#[C:38][Si](C)(C)C)=[CH:33][CH:32]=2)[CH3:30])[CH2:24][CH2:23]1>O1CCCC1>[C:37]([C:34]1[CH:33]=[CH:32][C:31]([C@@H:29]([N:25]2[CH2:24][CH2:23][C@:22]([CH2:21][C:20]([OH:19])([CH3:49])[CH3:50])([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[O:27][C:26]2=[O:28])[CH3:30])=[CH:36][CH:35]=1)#[CH:38]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66869815(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-trimethylsilylethynyl-phenyl)-ethyl]-[1,3]oxazinan-2-one

Product 1

HCID 86670541(S)-3-((S)-1-(4-ethynylphenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

nBu4NF (1 mol/L in tetrahydrofuran, 4.90 mL) was added to a solution of (S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-trimethylsilylethynyl-phenyl)-ethyl]-[1,3]oxazinan-2-one (2.00 g) in tetrahydrofuran (20 mL) at room temperature. The solution was stirred for 1 h at room temperature and then concentrated under reduced pressure. Ethyl acetate was added to the residue and the resulting mixture was washed with water and brine. The organic phase was dried (MgSO4) and the solvent was evaporated to afford the title compound as an oil that solidified on standing. Yield: 1.60 g (95% of theory); LC-MS (Method 1): tR=3.64 min; Mass spectrum (ESI+): m/z=378 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe resulting mixture was washed with water and brine
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c901cdf00d444534b545e4aa3499ab88
Source dataset
uspto-grants-2014_11
Patent number
US08883778B2

Reaction notes

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