HCID 66970991, compound → HCID 24904175, compound

HRID 1361523Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH2:15][CH:14]2[NH:16][CH:11]([CH2:12][CH2:13]2)[CH:10]=1>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:15][CH:14]2[NH:16][CH:11]([CH2:12][CH2:13]2)[CH2:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

Crude 10b from above (1.223 g) was dissolved in methanol (20 mL) and the solution purged with nitrogen gas for several minutes. 10% Palladium on carbon (500 mg, wet) was added and the flask flushed with nitrogen, followed by hydrogen (balloon). The reaction was heated at 60° C. for 1 h under a hydrogen balloon, then filtered through a pad of Celite and rinsed with methanol (3×25 mL). The filtrate was concentrated in vacuo to afford 1.030 g crude 3-(2-methoxyphenyl)-8-azabicyclo[3.2.1]octane 10c as a pale amber oil, which was taken to the next step without further purification. A small sample was purified via reverse-phase HPLC for analysis. 1H-NMR (400 MHz, DMSO-d6) δ 8.66 (br s, 2H), 7.33 (d, J=9.0 Hz, 1H), 7.23 (t, J=7.8 Hz, 1H), 6.99 (d, J=8.2 Hz, 1H), 6.93 (t, J=7.5 Hz, 1H), 4.00 (m, 2H), 3.80 (s, 3H), 3.34 (m, 1H), 2.35 (m, 2H), 1.99 (m, 2H), 1.86 (m, 2H), 1.78 (m, 2H). LC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 218.2 [M+H]+, retention time 1.81 min.

Workup

customthe solution purged with nitrogen gas for several minutes
addition10% Palladium on carbon (500 mg, wet) was added
customthe flask flushed with nitrogen
filtrationfiltered through a pad of Celite
washrinsed with methanol (3×25 mL)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-bf7824c3cd0e4ea896d6191ac4cda1bc
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880007B2

Reaction notes

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