4-Aminobenzyl alcohol → HCID 86714204, compound

HRID 1484207Notes

Reaction equation

HRID 1484207 reaction equation
[CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.C([N:13]([CH:16]([CH3:18])[CH3:17])[CH2:14]C)(C)C.[OH:19]N1C2C=CC=CC=2N=N1.NC1C=[CH:36][C:33]([CH2:34][OH:35])=[CH:32]C=1>C1COCC1>[CH:1]1([O:9][C:14](=[O:19])[NH:13][C:16]2[CH:17]=[CH:36][C:33]([CH2:34][OH:35])=[CH:32][CH:18]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 693314-Aminobenzyl alcoholHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12599566HCID 12599566, compound

Product 1

HCID 86714204HCID 86714204, compoundYield 159.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion, the PNP-derivative 34 derived from the major alcohol 31 (145 mg, 0.498 mmol) in 6.0 g THF, was reacted with diisopropylethylamine (210 mg, 1.63 mmol), 1-hydroxybenzotriazole (34 mg, 0.251 mmol) and 4-aminobenzylalcohol (128 mg, 1.04 mmol) for 3 days at ca. 30° C. Rotary evaporation and chromatography yielded the product major-35 as a viscous oil (110 mg, 0.40 mmol, 80%).

Workup

  1. customRotary evaporation and chromatography

Sources & evidence

ORD record
ord-e098d0bb0f8b42bc9e7a25105993d39e
Source dataset
uspto-grants-2016_08
Patent number
US09421274B2

Reaction notes

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