反应 #1597029

反应方程式

7-fluoro-2-methoxy-quinoline-8-carbaldehyde

(3R,6S)-[6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Water

LiHMDS

→

(E)-{(3R,6S)-6-[2-(7-fluoro-2-methoxy-quinolin-8-yl)-vinyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester

溶剂

DME

EA

反应条件

后处理

1. 1
   温度before warming slowly to rt
2. 2
   其他The two layers were decanted
3. 3
   萃取the aq. layer was extracted twice with EA (2×100 mL)
4. 4
   洗涤layers were washed with brine (100 mL)
5. 5
   干燥dried over MgSO4
6. 6
   浓缩concentrated to dryness
7. 7
   其他The residue (10.5 g) was carried on without further purification
8. 8
   其他The analytical data were obtained by trituration of a small portion of the crude in diethyl ether

实验过程

A mixture of 7-fluoro-2-methoxy-quinoline-8-carbaldehyde (5 g, 24.36 mmol; prepared according to WO 2008/126024) and (3R,6S)-[6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester (10.32 g, 24.36 mmol, prepared according to WO 2006/032466) in DME (104 mL) was cooled to −60° C. A solution of LiHMDS (1M in THF, 42 mL) was added drop wise over 30 min. The reaction was stirred 1 hour at this temperature before warming slowly to rt. Water (80 mL) and EA (80 mL) were added. The two layers were decanted and the aq. layer was extracted twice with EA (2×100 mL). The combined org. layers were washed with brine (100 mL), dried over MgSO4 and concentrated to dryness. The residue (10.5 g) was carried on without further purification. The analytical data were obtained by trituration of a small portion of the crude in diethyl ether.

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