반응 #85613

반응 방정식

NaBH4

N-methyl morpholine

ethyl chloroformate

sodium

(2S, 5R)-6-benzyloxy-7-oxo-1, 6-diaza-bicyclo [3.2.1] octane-2-carboxylic acid

→

(2S, 5R)-6-(benzyloxy)-2-(hydroxymethyl)-7-oxo-1,6-diaza-bicyclo[3.2.1] octane

수율 99.0%

(2S, 5R)-6-(benzyloxy)-2-(hydroxymethyl)-7-oxo-1, 6-diaza-bicyclo[3.2.1]octane

수율 99.0%

용매

tetrahydrofuran

ethyl acetate

water

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 1 hour at about −10° C
2. 2
   workup.STIRRINGunder stirring
3. 3
   workup.ADDITIONwas added to the reaction mass
4. 4
   workup.STIRRINGThe reaction mixture was stirred for 30 minutes
5. 5
   기타the layers were separated
6. 6
   세척Organic layer was washed with brine (200 ml)
7. 7
   기타The solvent was evaporated under vacuum to dryness

실험 절차

The sodium salt of (2S, 5R)-6-benzyloxy-7-oxo-1, 6-diaza-bicyclo [3.2.1] octane-2-carboxylic acid (II) (50 g, 0.16 moles, prepared as per the procedure described in Indian Patent Application No. 699/MUM/2013) was suspended in tetrahydrofuran (500 ml). To the suspension was added N-methyl morpholine (18.4 ml, 0.16 moles) under stirring. The reaction mixture was cooled to about −10° C. and ethyl chloroformate was added via addition funnel and stirred for 1 hour at about −10° C. To the reaction mixture was added NaBH4 (9.56 g, 0.25 moles) in lots under stirring. The reaction was monitored with the help of thin layer chromatography (TLC). After completion of reaction, water (500 ml) followed by ethyl acetate (500 ml) was added to the reaction mass. The reaction mixture was stirred for 30 minutes and the layers were separated. Organic layer was washed with brine (200 ml). The solvent was evaporated under vacuum to dryness to provide 43 g of (2S, 5R)-6-(benzyloxy)-2-(hydroxymethyl)-7-oxo-1,6-diaza-bicyclo[3.2.1] octane (III) as a pale yellow oil (99% yield).

출처