Ether hydrochloride → HCID 68611946, compound

HRID 2095302Notes

Reaction equation

HRID 2095302 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][OH:31])[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][OH:31])[CH:23]=[N:24][CH:25]=1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 68611901HCID 68611901, compound

Product 1

HCID 68611946HCID 68611946, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2M anhydrous HCl/ether (2.0 mL) was added to a stirred solution of 2-[(1S,2R)-2-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]cyclopropyl]ethanol (200 mg, 0.57 mmol) in dry MeOH (2.0 mL) at 0° C. The mixture was stirred at room temperature for 12 h and concentrated, and the residue was purified by HPLC to obtain pure 2-[(1S,2R)-2-[5-[(2(S)-azetidinyl)methoxy]-3-pyridyl]cyclopropyl]ethanol hydrochloride (115 mg). 1H NMR (CD3OD, 400 MHz) δ 8.53 (s, 1H), 8.37 (s, 1H), 7.99 (s, 1H), 5.05-4.90 (m, 1H), 4.75-4.51 (m, 2H), 4.23-4.05 (m, 2H), 3.76-3.64 (m, 2H), 2.83-2.59 (m, 2H), 2.11-1.99 (m, 1H), 1.79-1.58 (m, 2H), 1.55-1.39 (m, 1H), 1.34-1.23 (m, 1H), 1.21-1.09 (m, 1H). MS m/z (ESI) 271 (M+Na+).

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-fff1674a11b74ead98a6d0e159f2859d
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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