A new, economical, practical and racemization-free method for the reductive removal of 2-oxazolidinones from N-acyloxazolidinones with sodium borohydride

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7067-7070

  Prashad, Mahavir ^a   Har, Denis ^a   Kim, Hong Yong ^a   Repic, Oljan ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; SODIUM BOROHYDRIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; REDUCTION;

EID: 0032563845     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01521-4     Document Type: Article

References (13)

1. 1. Evans, D. A. Aldrichimica Acta 1982, 15, 23-32.
2. 2. Ager, J. A.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997, 30, 3-12.
3. 3. Ager, J. A.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
4. 4. Fukuzawa, S.; Hongo, Y. Tetrahedron Lett. 1998, 39, 3521-3524.
5. 5. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
6. 6. Barnett, C. J.; Wilson, T. M.; Evans, D. A.; Somers, T. C. Tetrahedron Lett. 1997, 38, 735-738.
7. 7. Penning, T. D.; Djuric, S. W.; Haack, R. A.; Kalish, V. J.; Miyashiro, J. M.; Rowell, B. W.; Yu, S. S. Synth. Commun. 1990, 20, 307-312.
8. 8. Brown, M. S.; Rapoport, H. J. Org. Chem. 1963, 28, 3261-3263.
9. 9. Bianco, A.; Passacantilli, P.; Righi, G. Synth. Commun. 1988, 18, 1765-1771.
10. 10. Typical procedure: To a mixture of the starting material (29.6 mmol) in THF (90 mL) was added a solution of sodium borohydride (118.5 mmol; 4 equivalents) in water (28 mL) at a rate to maintain the internal temperature at 20-25 °C. The mixture was stirred at room temperature for 1-6 h, and the completion of the reaction was monitored by tlc. To the reaction mixture was added 2 N HCl (80 mL) at a rate to maintain the internal temperature at 20-25 °C. The reaction mixture was extracted with ethyl acetate (2 × 150 mL). The combined organic layers were washed with brine (150 mL), concentrated under vacuum, and purified by silica gel chromatography.
11. 11. All the compounds gave satisfactory spectral data.
12. 12. The starting materials were available by known chemistry. For cyanomethylation also see Azam, S.; D'Souza, A. A.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1996, 621-627.
13. 13. The optical purities were determined by chiral HPLC method on a Rainin Dynamax system using a Daicel Chiralcel OJ column (4.6 × 250 mm) and a mixture of hexane : ethanol : TFA (93 : 7 : 0.1 mL) as the mobile phase (isocratic at a flow rate of 1 mL/min and UV detector at 260 nm) for compounds 14 and 15; and a Daicel Chiralpak AD column (4.6 × 250 mm) and a mixture of hexane : ethanol : methanol : TFA (96 : 2 : 2 : 0.1 mL) as the mobile phase (isocratic at a flow rate of 0.8 mL/min and UV detector at 254 nm) at 30 °C for 16 and 17.