Ethanolamine → 3-Benzyloxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one

HRID 1906182Notes

Reaction equation

HRID 1906182 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C(=O)C=COC=1C)C1C=CC=CC=1.C(N1C=CC(=O)C(O)=C1C)(=O)C.[NH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][OH:51].OCCN>>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:45]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][OH:51])[C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 700EthanolamineHCID 756345-Aminopentan-1-olHCID 14901193-Benzyloxy-2-methyl-4-pyroneHCID 867413491-acetyl-3-hydroxy-2-methylpyrid-4-one 3-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 133367163-Benzyloxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one

Procedure

3-Benzyloxy-2-methyl-4-pyrone, prepared as described under (J), is reacted with 1-amino-5-hydroxypentane under substantially similar conditions to those described under (K) for reaction with 2-hydroxyethylamine to give 3-benzyloxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one. This is deprotected using the procedure described under (I) to give 3-hydroxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one as white crystals, m.p. 136°-138° C.; δmax (nujol) 1625, 3350 cm-1 : δ(d6DMSO) 1.3 (m, 6H), 2.40 (s, 3H), 3.25 (t, 2H), 4.20 (t, 2H), 7.20 (d, 1H), 8.15 (d, 1H).

Sources & evidence

ORD record
ord-0f77fb55050b41e1b2c1baf9ec8c0595
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

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