Synthesis of LY311727

Structure of LY311727

C22H27N2O5P

Principal investigator	Michael J. Martinelli
Publication year	1996
Synthesis type	Total
Number of steps	8 (linear)
References	J. Org. Chem. 1996, 61, 9055.

Part 1 of 1

intermediate structure

+

intermediate structure

MeNO2

RT, 2 d, 52%

See the Nenitzescu Indole Synthesis

intermediate structure

MeI, n-Bu4N+ Br-, NaOH

H2O

Reflux, 30 min, 80%

intermediate structure

LiAlH4

THF

0 °C, 4 h, 78%

intermediate structure

TMSCN, BF3.OEt2

CH2Cl2

0 °C, 60 min, 83%

intermediate structure

KOH

t-BuOH

Reflux, 60 min, 85%

intermediate structure

BBr3

CH2Cl2

0 °C, 2 h, 80%

intermediate structure

+

intermediate structure

n-Bu4N+ Br-, KOH, K2CO3

DMF

RT, 16 h, 89%

intermediate structure

TMSI

CH2Cl2

RT, 90 min, 92%

intermediate structure

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