Trolox → (6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)(4-hydroxypiperidin-1-yl)methanone

HRID 2428238Notes

Reaction equation

HRID 2428238 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=O)[CH2:6][CH2:5]2.C1N=CN(C(N2C=NC=C2)=O)C=1.[OH:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([C:14]([N:35]1[CH2:36][CH2:37][CH:32]([OH:31])[CH2:33][CH2:34]1)=[O:16])([CH3:17])[CH2:6][CH2:5]2

Participants

4

Reactant 3

HCID 40634TroloxHCID 682631,1'-CarbonyldiimidazoleHCID 79341Piperidin-4-ol

Product 1

HCID 67263066(6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)(4-hydroxypiperidin-1-yl)methanoneYield 33.3%

Procedure

Following the amide coupling procedure described in protocol A, 500 mg 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (2.0 mmol), 370 mg CDI (2.28 mmol) and 222 mg 4-hydroxypiperidine (2.20 mmol) produced 222 mg of a (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)(4-hydroxypiperidin-1-yl)methanone as a white foam.

Sources & evidence

ORD record
ord-5ab6444aae894e19821f0a083db33f63
Source dataset
uspto-grants-2011_06
Patent number
US07968746B2

Reaction notes

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