Phenol → HCID 68108517, compound

HRID 2179441Notes

Reaction equation

[CH2:1]([C:8]1[CH:9]=[C:10](Cl)[C:11]2[O:20][C:19]3[CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][C:14]=3[C:12]=2[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([OH:35])C=CC=CC=1>>[CH2:1]([C:8]1[CH:9]=[C:10]([OH:35])[C:11]2[O:20][C:19]3[CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][C:14]=3[C:12]=2[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 996Phenol

HCID 68109257HCID 68109257, compound

Product 1

HCID 68108517HCID 68108517, compoundYield 71%

Procedure

The product of step C (150 mg, 0.37 mmol) was converted to the phenol derivative following the procedure of Example 54, step A. The crude product was purified by column chromatography (SiO2, 4:1 hexanes/ethyl acetate) providing tert-butyl 8-benzyl-6-hydroxy-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (100 mg, 71%) as an off-white solid which was converted directly to the methyl ether derivative following the procedure of Example 54, step B. Purification by column chromatography (SiO2, 85:15 hexanes/ethyl acetate) provided tert-butyl 8-benzyl-6-methoxy-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (80 mg, 58%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 7.32-7.27 (m, 2H), 7.23-7.16 (m, 3H), 6.84 (br s, 1H), 6.61 (s, 1H), 4.50 (br s, 2H), 4.04 (s, 2H), 3.95 (s, 3H), 3.80 (t, J=5.4 Hz, 2H), 2.88-2.81 (m, 2H), 1.49 (s, 9H).

Workup

customThe crude product was purified by column chromatography (SiO2, 4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-36804e55fcae4cc3be3e11f05516709e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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