Ether hydrochloride → HCID 68612302, compound

HRID 2095300Notes

Reaction equation

HRID 2095300 reaction equation
[ClH:1].CCOCC.C(OC([N:14]1[CH2:17][CH2:16][C@H:15]1[CH2:18][O:19][C:20]1[CH:21]=[C:22]([C@H:26]2[CH2:28][C@@H:27]2[CH2:29][CH2:30][CH2:31][CH2:32][OH:33])[CH:23]=[N:24][CH:25]=1)=O)(C)(C)C>CO>[ClH:1].[NH:14]1[CH2:17][CH2:16][C@H:15]1[CH2:18][O:19][C:20]1[CH:21]=[C:22]([C@H:26]2[CH2:28][C@@H:27]2[CH2:29][CH2:30][CH2:31][CH2:32][OH:33])[CH:23]=[N:24][CH:25]=1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 68611724HCID 68611724, compound

Product 1

HCID 68612302HCID 68612302, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2M anhydrous HCl/ether (2.0 mL) was added to a stirred solution of 4-[(1S,2S)-2-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]cyclopropyl]-1-butanol (200 mg, 0.53 mmol) in dry MeOH (2.0 mL) at 0° C. The mixture was stirred at room temperature for 12 h. The above solution was concentrated in vacuo and purified by HPLC to obtain 4-[(1S,2S)-2-[5-[(2(S)-azetidinyl)methoxy]-3-pyridyl]cyclopropyl]-1-butanol hydrochloride (128 mg). 1H NMR (CD3OD, 300 MHz) δ 8.25 (br s, 2H), 7.51 (s, 1H), 5.02-4.93 (m, 2H), 4.55-4.38 (m, 2H), 4.21-4.00 (m, 2H), 3.56 (t, 2H, J=6.2 Hz), 2.82-2.55 (m, 2H), 1.93-1.75 (m, 1H), 1.70-1.36 (m, 6H), 1.33-1.17 (m, 1H), 1.16-1.06 (m, 1H), 1.05-0.93 (m, 1H). MS (ESI) m/z 277 (M+H+).

Workup

  1. concentrationThe above solution was concentrated in vacuo
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-7d84f59081b24179ab3e903459480ca1
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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