Triethylamine → (+)-(1S,2S)-3-formyl-2-methyl-8-(2-hydroxy-1,2,3,4-tetrahydro-1-naphthyloxy)-imidazo[1,2-a]pyridine

HRID 1195734Notes

Reaction equation

HRID 1195734 reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:12])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2].C(N([CH2:19][CH3:20])CC)C>CO>[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][C@H:6]3[C:19]4[C:20](=[CH:1][CH:3]=[CH:4][CH:13]=4)[CH2:9][CH2:10][C@@H:11]3[OH:12])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 232941873-Formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 57272523(+)-(1S,2S)-3-formyl-2-methyl-8-(2-hydroxy-1,2,3,4-tetrahydro-1-naphthyloxy)-imidazo[1,2-a]pyridineYield 47.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

580 mg of 3-formyl-8-hydroxy-2-methyl-imidazo[1,2-a]pyridine and 580 mg of (+)-1R,2S-1,2,3,4-tetrahydro-naphthaline-1,2-oxide are reacted, analogously to the method described in Example 21, with 340 mg triethylamine in 43 ml of aqueous methanol (35 ml methanol+8 ml water) at 60° C. After 8 hours the mixture is worked up as described in Example 41. After stirring with petroleum ether and drying in high vacuum, 250 mg of the title compound is isolated. [α]D22 =+38° (c=1, chloroform).

Workup

  1. customdrying in high vacuum

Sources & evidence

ORD record
ord-b907ca6cbe124c2dbb01347c95236af0
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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