HCID 59371468, compound → HCID 59371286, compound

HRID 2095329Notes

Reaction equation

HRID 2095329 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]([CH:35]=[CH:36][CH:37]=2)[CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[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]([CH:35]=[CH:36][CH:37]=2)[CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:31])[CH3:32])[CH:20]=[N:21][CH:22]=1

Participants

4

Reactant 1

HCID 59371468HCID 59371468, compound

Product 1

HCID 59371286HCID 59371286, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 100 mL round-bottom flask with magnetic stirrer and H2 balloon, tert-butyl [3-[5-[[1-(benzyloxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]benzyl]carbamate (91.2 mg, 181 μmol) in MeOH (3 mL) was stirred with 10% Pd/C (19 mg; Alfa Aesar #38305, water content 50%) at room temperature for 2.5 h. H2 was replaced with Ar, and the catalyst was filtered off over a cotton plug and rinsed with MeOH (1.5 mL). The solution was evaporated and dried (35° C., oil pump vacuum) to yield the free azetidine (67.3 mg, 101%, must contain a trace of solvent) as a colorless film. [α]D0, [α]5460 (c 6.4 g/L, MeOH). 1H NMR (CDCl3, 500 MHz) δ 8.46 (br s, 1H), 8.32 (br s, 1H, J=2.8 Hz), 7.51-7.34 (m, 5H), 4.98 (br, 1H), 4.42 (narrow m, 1H), 4.34 (m, 1H), 4.18-4.08 (m, 2H), 3.75 (q, 1H, J=7.9 Hz), 3.50 (m, 1H), 2.44 (m, 1H), 2.33 (m, 1H), 1.89 (br, 2H), 1.49 (s, 9H). MS (EI) m/z 369 (M+, 0.1%), 314 (15%), 313 (21%), 257 (23%), 214 (24%), 213 (11%), 70 (11%), 56 (100%).

Workup

  1. filtrationthe catalyst was filtered off over a cotton plug
  2. washrinsed with MeOH (1.5 mL)
  3. customThe solution was evaporated
  4. customdried (35° C., oil pump vacuum)

Sources & evidence

ORD record
ord-7cd55adf80a440f18b5e3cc7d39f6651
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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