Benzyl Alcohol → HCID 69425031, compound

HRID 1351752Notes

Reaction equation

HRID 1351752 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][C:6]1([CH2:23][CH2:24][CH3:25])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([OH:21])[C:14]=3[CH3:22])C.[CH3:27][C:28](C)(C)[CH2:29]CO.FC1C=C(C=CC=1)CO.C(O)C1C=CC=CC=1.[OH-].[Na+]>CCO.C(O)CCC.C(O)(C)C.CO>[C:19]([C:17]1[CH:16]=[C:15]([O:21][CH2:27][CH2:28][CH3:29])[C:14]([CH3:22])=[C:13]2[C:18]=1[C:10]1[CH2:9][CH2:8][O:7][C@:6]([CH2:5][C:4]([OH:3])=[O:26])([CH2:23][CH2:24][CH3:25])[C:11]=1[NH:12]2)#[N:20]

Participants

10

Reactant 5

HCID 244Benzyl AlcoholHCID 122333,3-Dimethyl-1-butanolHCID 14798Sodium HydroxideHCID 680083-Fluorobenzylic alcoholHCID 69381055HCID 69381055, compound

Product 1

HCID 69425031HCID 69425031, compound

Reagents, catalysts & solvents 4

HCID 2631-ButanolSolventHCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

Examples 362–368 were synthesized following the above mentioned procedure for example 359 using the intermediate (5-cyano-7-hydroxy-8-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester and coupling it with the following alcohols: ethanol, methanol, isopropanol, n-butyl alcohol, 3,3-dimethyl-1-butanol, 3-fluorobenzyl alcohol, and benzyl alcohol. The resulting esters were hydrolyzed using 10% NaOH (aq) in EtOH.

Workup

  1. customExamples 362–368 were synthesized

Sources & evidence

ORD record
ord-b41c4f9b49f744718f0f1d1e7f8beb95
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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