반응 #1885043

반응 방정식

sodium potassium tartaric acid

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

aniline

trimethylaluminum

→

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

수율 78.4%

용매

DCM

DCM

반응 조건

후처리

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

실험 절차

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.

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