Tryptophol → 1-(Acetamidomethyl)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

HRID 647586

Reaction equation

HRID 647586 reaction equation
N1C2C(=CC=CC=2)C(CCO)=C1.C(C1C=CC=C2C=1NC=C2CCO)C.COC1C=C2C(C(CCO)=CN2)=CC=1.C1(COC2C=C3C(=CC=2)NC=C3CCO)C=CC=CC=1.C([C:63]1[CH:64]=[CH:65][CH:66]=[C:67]2[C:71]=1[NH:70][C:69]1[C:72]([CH2:77][NH:78][C:79](=[O:81])[CH3:80])([CH3:76])[O:73][CH2:74][CH2:75][C:68]2=1)C.COC1C=C2C(C3CCOC(CNC(=O)C)(C)C=3N2)=CC=1.C1(COC2C=C3C(=CC=2)NC2C(CNC(=O)C)(C)OCCC3=2)C=CC=CC=1>>[CH3:76][C:72]1([CH2:77][NH:78][C:79](=[O:81])[CH3:80])[C:69]2[NH:70][C:71]3[C:67]([C:68]=2[CH2:75][CH2:74][O:73]1)=[CH:66][CH:65]=[CH:64][CH:63]=3

Participants

8

Reactant 7

HCID 10685TryptopholHCID 1982317-EthyltryptopholHCID 7448495-Benzyloxy-3-(2-hydroxyethyl)indoleHCID 20485044N-[(7-methoxy-1,3,4,9-tetrahydro-1-methylpyrano-[3,4-b]indol-1-yl)methyl]-acetamideHCID 20485069N-[(8-ethyl-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-acetamideHCID 204851012-(6-Methoxy-1h-indol-3-yl)ethanolHCID 20485103N-[(6-phenylmethoxy-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-acetamide

Product 1

HCID 127081801-(Acetamidomethyl)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

Procedure

In the same manner but replacing indole-3-ethanol with an equivalent amount of 7-ethylindole-3-ethanol, 6-methoxyindole-3-ethanol or 5-phenylmethoxy-indole-3-ethanol, the following compounds of formula IIa are obtained, respectively: N-[(8-ethyl-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-acetamide, N-[(7-methoxy-1,3,4,9-tetrahydro-1-methylpyrano-[3,4-b]indol-1-yl)methyl]-acetamide and N-[(6-phenylmethoxy-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-acetamide.

Workup

  1. customthe following compounds of formula IIa are obtained

Sources & evidence

ORD record
ord-cf108d1e3bac41459f0d9bd66c321af4
Source dataset
uspto-grants-1983_10
Patent number
US04409224

Linked notes

Loading…