Ethyl Acetate → (s)-2-(n-Boc-n-methylamino)-1-(tert-butyldimethylsilyloxy)-but-3-yne

HRID 366751Notes

Reaction equation

HRID 366751 reaction equation
[C:1]([NH:8][C@@H:9]([C:19]#[CH:20])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH3:23]COC(C)=O>C1COCC1>[C:1]([N:8]([C@@H:9]([C:19]#[CH:20])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH3:23])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 21971752(S)-N-Boc-2-amino-1(-tert-butyldimethylsilyloxy)-but-3-yne

Product 1

HCID 21971751(s)-2-(n-Boc-n-methylamino)-1-(tert-butyldimethylsilyloxy)-but-3-yne

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-(N-Boc-N-Methylamino)-1-(-tert-butyldimethylsilyloxy)-but-3-yne was synthesized according to Method Y above by the treatment of (S)-N-Boc-2-amino-1-(-tert-butyldimethylsilyloxy)-but-3-yne (190 mg, 0.64 mmol) (Example 115B) with NaH (18 mg, 0.76 mmol) and Mel (180 mg, 1.27 mmol) in THF (5 mL). The product was obtained after silica gel column chromatography with a 0-10% EtOAc in hexanes gradient. (Yield 190 mg, 95%).

Sources & evidence

ORD record
ord-9dfafa6150644b8cb75237220509f89c
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

Loading…