HCID 59371635, compound → HCID 59371305, compound

HRID 2095328Notes

Reaction equation

HRID 2095328 reaction equation
C(OC([N:11]1[CH2:14][CH2:13][C@H:12]1[CH2:15][O:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:24]=[C:25]([CH2:29][CH2:30][OH:31])[CH:26]=[CH:27][CH:28]=2)[CH:20]=[N:21][CH:22]=1)=O)C1C=CC=CC=1>CO.[Pd]>[NH:11]1[CH2:14][CH2:13][C@H:12]1[CH2:15][O:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:24]=[C:25]([CH2:29][CH2:30][OH:31])[CH:26]=[CH:27][CH:28]=2)[CH:20]=[N:21][CH:22]=1

Participants

4

Reactant 1

HCID 59371635HCID 59371635, compound

Product 1

HCID 59371305HCID 59371305, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

In a 100 mL round-bottom flask with magnetic stirrer and H2 balloon, 2-[3-[5-[[1-(benzyloxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]phenyl]ethanol (240 mg, 574 μmol) in MeOH (10 mL) was stirred with 10% Pd/C (50 mg; Alfa Aesar #38305, water content 50%) at room temperature for 130 min. H2 was replaced with Ar, and the catalyst was filtered off over a cotton plug and rinsed with MeOH (2 mL). The solution was evaporated and dried (30° C., oil pump vacuum) to yield the free base as a colorless film. [α]D−1.0, [α]546−1.4 (c 7.35 g/L, MeOH). 1H NMR (CDCl3, TMS, 400 MHz) δ 8.41 (d, 1H, J=1.8 Hz), 8.28 (d, 1H, J=2.8 Hz), 7.45-7.40 (m, 3H), 7.39 (dd, 1H, J=1.8, 2.8 Hz), 7.28 (dt, 1H, J=6.4 Hz (d), 2.1 Hz (t)), 4.31 (m, 1H), 4.12, 4.08 (ABq, 2H, J=9.4 Hz, low-field part d with J=6.2 Hz, high-field part d with J=4.8 Hz), 3.92 (t, 2H, J=6.6 Hz), 3.72 (q, 1H, J=7.9 Hz), 3.48 (m, 1H), 2.95 (t, 2H, J=6.6 Hz), 2.41, 2.29 (ABq, 2H, J=11.0 Hz, low-field part m, high-field part q with J=8.2 Hz), 2.08 (br, NH, OH, and H2O). MS (EI) m/z 284 (M+, 1.9%), 254 (2.2%), 229 (36%), 228 (56%), 199 (10%), 56 (100%).

Workup

  1. filtrationthe catalyst was filtered off over a cotton plug
  2. washrinsed with MeOH (2 mL)
  3. customThe solution was evaporated
  4. customdried (30° C., oil pump vacuum)
  5. customto yield the free base as a colorless film

Sources & evidence

ORD record
ord-883760e93b0c465d905188f21c9ca907
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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