Reaction #1885043

Reaction equation

sodium potassium tartaric acid

(R)-3-(tert-butyldiphenylsilyloxy)-dihydrofuran-2(3H)-one

aniline

trimethylaluminum

→

(R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide

Yield 78.4%

Solvents

DCM

DCM

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction mixture was stirred at RT for 16 hours
2. 2
   workup.STIRRINGstirred for 15 min
3. 3
   OtherThe layers were separated
4. 4
   Washthe aqueous layer was washed with DCM (4×)
5. 5
   WashThe combined organics were washed with 0.1M HCl (2×), brine
6. 6
   Dryingdried over Na2SO4
7. 7
   Otherevaporated to dryness
8. 8
   OtherPurification by silica gel chromatography (10-30% EtOAc in hexane)

Procedure

To a solution of aniline (356 mg, 348 μL, 3.82 mmol) in DCM (17 mL) was added trimethylaluminum (2.0M, 2.1 mL, 4.2 mmol) dropwise and the reaction mixture was stirred at RT for 40 min. A solution of (R)-3-(tert-butyldiphenylsilyloxy)-dihydrofuran-2(3H)-one (1.00 g, 2.94 mmol) in DCM (12 mL) was added dropwise and the reaction mixture was stirred at RT for 16 hours. The reaction mixture was poured into a saturated solution of sodium potassium tartaric acid and stirred for 15 min. The layers were separated, and the aqueous layer was washed with DCM (4×). The combined organics were washed with 0.1M HCl (2×), brine, dried over Na2SO4 and evaporated to dryness. Purification by silica gel chromatography (10-30% EtOAc in hexane) afforded the (R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide (1.00 g, 78%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=434.7; tR=2.16 min.

Source