2-Bromo-4-methoxyphenol → Tert-butyl 6-hydroxy-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

HRID 1616905Notes

Reaction equation

HRID 1616905 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]2[CH:8]3[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.C(N1CC=CC(O)C1)(OC(C)(C)C)=[O:23].BrC1C=C(OC)C=CC=1O>>[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]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13][CH:8]3[C:5]=2[CH:6]=1

Participants

4

Reactant 3

HCID 2973822-Bromo-4-methoxyphenolHCID 177501313-Hydroxy-1,2,3,6-tetrahydropyridine, N-BOC protectedHCID 67325270Tert-butyl 7-hydroxy-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

Product 1

HCID 68305717Tert-butyl 6-hydroxy-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

Procedure

Tert-butyl 6-hydroxy-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate was synthesized as described for tert-butyl 7-hydroxy-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate starting N-boc-3-hydroxy-1,2,3,6-tetrahydropyridine and 2-bromo-4-methoxyphenol.

Sources & evidence

ORD record
ord-bfa0669c00b545b0839efe41a04e47ee
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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