Methanol → HCID 131719689, compound

HRID 565476Notes

Reaction equation

HRID 565476 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[N:15]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17][CH2:16]2.[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].CO>C(OCC)(=O)C>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][CH:16]3[CH2:17][CH2:18][CH:19]4[CH2:22][CH2:23][N:15]3[CH2:21][CH2:20]4)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 971Oxalic AcidHCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 179455751-Azabicyclo[3.2.2]nonane

Product 1

HCID 131719689HCID 131719689, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 1-azabicyclo[3.2.2]nonane. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 85% overall yield. FDMS m/e=314 (M+ of free base). α[D]589=−20.39 (c=0.48, methanol).

Sources & evidence

ORD record
ord-8bcd0178526e455a907a9b717b1162f8
Source dataset
uspto-grants-2001_01
Patent number
US06172073B2

Reaction notes

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