2'-Hydroxy-3'-methoxyacetophenone → tert-butyl 6-hydroxy-4a-methyl-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

HRID 1616925

Reaction equation

HRID 1616925 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH3:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]3[O:21][C:4]=2[CH:3]=1.[OH:23]C1C(OC)=CC=CC=1C(=O)C>>[OH:23][C:7]1[CH:2]=[CH:3][C:4]2[O:21][CH:9]3[CH2:10][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:12][CH2:13][C:8]3([CH3:22])[C:5]=2[CH:6]=1

Participants

3

Reactant 2

HCID 959932'-Hydroxy-3'-methoxyacetophenoneHCID 68304817Tert-butyl 7-hydroxy-4a-methyl-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

Product 1

HCID 68304691tert-butyl 6-hydroxy-4a-methyl-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

Procedure

Synthesized as described for tert-butyl 7-hydroxy-4a-methyl-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate and as described in J. Med. Chem., 1989, 32, 2221-2226 starting from 1-(2-hydroxy-3-methoxyphenyl)-ethanone. MS m/z 250 [M-tBu+H]+

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-aa31bad2a93b43c88cd7ae72556ca5c1
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Linked notes

Loading…