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Volumn 61, Issue 26, 1996, Pages 9564-9568

Unique and efficient synthesis of [2S-(2R*,3S*,4R*)]-2-amino-1-cyclohexyl-6-methyl-3,4- heptanediol, a popular C-terminal component of many renin inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 CYCLOHEXYL 6 METHYL 3,4 HEPTANEDIOL; ALKANEDIOL DERIVATIVE; RENIN INHIBITOR; UNCLASSIFIED DRUG;

EID: 0030462372     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960694n     Document Type: Article
Times cited : (41)

References (37)
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    • The longer reaction and workup times involved in a large scale reaction were a concern for epimerization. On a 20 kg scale, a 42% yield was obtained for the combined reaction steps preparing 3 and 4. We believe the lower large scale yield was also due to larger than expected amounts of the corresponding alcohol present arising from overreduced aldehyde 3. Both of these factors contributed to the lower isolation yield in the crystallization process of 4. Pursuit in optimizing the scale-up process of this reaction was dropped due to finding a commercial kilogram quantity source for 5 (Nippon Kayaku Co., Ltd.).
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