Hydrochloric Acid → 1-[3-[5-[(2(S)-Azetidinyl)methoxy]-3-pyridyl]phenyl]-3-phenyl-2(R)-propanol Hydrochloride

HRID 2095351Notes

Reaction equation

HRID 2095351 reaction equation
[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:14]=[C:15]([CH2:19][C@H:20]([OH:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=[CH:17][CH:18]=2)[CH:10]=[N:11][CH:12]=1.[ClH:29]>CO>[ClH:29].[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:14]=[C:15]([CH2:19][C@H:20]([OH:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=[CH:17][CH:18]=2)[CH:10]=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 461913501-[3-[5-[(2(S)-azetidinyl)methoxy]-3-pyridyl]phenyl]-3-phenyl-2(R)-propanol

Product 1

HCID 686116921-[3-[5-[(2(S)-Azetidinyl)methoxy]-3-pyridyl]phenyl]-3-phenyl-2(R)-propanol Hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[3-[5-[(2(S)-azetidinyl)methoxy]-3-pyridyl]phenyl]-3-phenyl-2(R)-propanol (130 mg, 0.35 mmol) in methanol (1 mL) was added 2M hydrochloric acid (0.4 mL) at 0° C. under N2. The solution was stirred for 2 h at room temperature and then evaporated. Water (8 mL) was added to dissolve the residue, and the solution was lyophilized. The residue was dissolved in 12 mL of water, and the solution was re-lyophilized to give the hydrochloride (145 mg) as a colorless solid. 1H NMR (D2O, 300 MHz) δ 8.65 (s, 1H), 8.51 (s, 1H), 8.38 (s, 1H), 7.58-7.47 (m, 3H), 7.42-7.39 (m, 1H), 7.32-7.22 (m, 5H), 4.99-4.94 (m, 1H), 4.57 (d, 2H, J=3.9 Hz), 4.17-4.03 (m, 3H), 2.99-2.63 (m, 6H). Anal. Calcd. for C24H26N2O2.2.45HCl.1.65H2O: C, 58.41; H, 6.48; N, 5.68; Cl, 17.60. Found: C, 58.51; H, 6.69; N, 5.58; Cl, 17.66.

Workup

  1. customevaporated
  2. additionWater (8 mL) was added
  3. dissolutionto dissolve the residue
  4. dissolutionThe residue was dissolved in 12 mL of water

Sources & evidence

ORD record
ord-2e0ae21241884541b7ef7f57e3fef291
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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