Racemic Synthesis of a Key 1,4-Dihydro-2H-spiro[isoquinoline-3,4′- piperidin]-3′-ol Building Block

David A. Candito; Theodore A. Martinot; Jing Su; Josep Sauri; Yu-hong Lam; Leo A. Joyce; Steven M. Silverman; David L. Sloman; Matthew L. Maddess; Michelle R. Macha

doi:10.1021/acs.oprd.2c00121

Racemic Synthesis of a Key 1,4-Dihydro-2H-spiro[isoquinoline-3,4′- piperidin]-3′-ol Building Block

David A. Candito
, Theodore A. Martinot
, Jing Su
, Josep Sauri
, Yu-hong Lam
, Leo A. Joyce
, Steven M. Silverman
, David L. Sloman
, Matthew L. Maddess
, Michelle R. Macha

Producció científica: Article en revista indexada › Article › Avaluat per experts

1 Citació (Scopus)

Resum

The synthesis of a key spiroamine building block for a medicinal chemistry program is described. Key innovations were a regioselective epoxide ring opening and a late-stage Pictet-Spengler reaction that was quickly optimized using Design of Experiments.

Idioma original	Anglès
Pàgines (de-a)	3034-3041
Nombre de pàgines	8
Revista	Organic Process Research & Development
Volum	26
Número	11
Data online anticipada	8 de nov. 2022
DOIs	https://doi.org/10.1021/acs.oprd.2c00121
Estat de la publicació	Publicada - 18 de nov. 2022
Publicat externament	Sí

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10.1021/acs.oprd.2c00121

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title = "Racemic Synthesis of a Key 1,4-Dihydro-2H-spiro[isoquinoline-3,4′- piperidin]-3′-ol Building Block",

abstract = "The synthesis of a key spiroamine building block for a medicinal chemistry program is described. Key innovations were a regioselective epoxide ring opening and a late-stage Pictet-Spengler reaction that was quickly optimized using Design of Experiments.",

keywords = "Design of Experiments, Chemoselective, Drug discovery, Regioselective, Spirocycles",

author = "Candito, \{David A.\} and Martinot, \{Theodore A.\} and Jing Su and Josep Sauri and Yu-hong Lam and Joyce, \{Leo A.\} and Silverman, \{Steven M.\} and Sloman, \{David L.\} and Maddess, \{Matthew L.\} and Macha, \{Michelle R.\}",

year = "2022",

month = nov,

day = "18",

doi = "10.1021/acs.oprd.2c00121",

language = "English",

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journal = "Organic Process Research \& Development",

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AU - Candito, David A.

AU - Martinot, Theodore A.

AU - Su, Jing

AU - Sauri, Josep

AU - Lam, Yu-hong

AU - Joyce, Leo A.

AU - Silverman, Steven M.

AU - Sloman, David L.

AU - Maddess, Matthew L.

AU - Macha, Michelle R.

PY - 2022/11/18

Y1 - 2022/11/18

N2 - The synthesis of a key spiroamine building block for a medicinal chemistry program is described. Key innovations were a regioselective epoxide ring opening and a late-stage Pictet-Spengler reaction that was quickly optimized using Design of Experiments.

AB - The synthesis of a key spiroamine building block for a medicinal chemistry program is described. Key innovations were a regioselective epoxide ring opening and a late-stage Pictet-Spengler reaction that was quickly optimized using Design of Experiments.

KW - Design of Experiments

KW - Chemoselective

KW - Drug discovery

KW - Regioselective

KW - Spirocycles

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JO - Organic Process Research & Development

JF - Organic Process Research & Development

IS - 11

ER -

Racemic Synthesis of a Key 1,4-Dihydro-2H-spiro[isoquinoline-3,4′- piperidin]-3′-ol Building Block

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