Hydrochloric Acid → HCID 69831504, compound

HRID 1780344Notes

Reaction equation

HRID 1780344 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([O:19][CH2:20][C@H:21]3[CH2:25][CH2:24][CH2:23][N:22]3C(OC(C)(C)C)=O)[CH:10]=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:33]>O1CCOCC1>[ClH:33].[ClH:33].[C:1]1([C:7]2[CH:8]=[C:9]([O:19][CH2:20][C@H:21]3[CH2:25][CH2:24][CH2:23][NH:22]3)[CH:10]=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22872660HCID 22872660, compound

Product 1

HCID 69831504HCID 69831504, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the 5,6-diphenyl-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine compound from Example 69b (140 mg) was added HCl in dioxane (3 mL). The mixture was stirred at room temperature for 40 hours. The solvent was removed under vacuum at 50° C., and the residue was triturated with ether. The solid was dried under high vacuum to afford the title compound. MS (DCI/NH3) m/z 331 (M+H)+. 1 H NMR (D2O, 300 MHz) δ: 1.97.-2.20 (m, 3H), 2.33 (m, 1H), 3.43 (t, J=7.2 Hz, 1H), 3.74 (m, 1H), 4.21 (m, 1H), 4.48 (m, 1H), 4.68 (dd, J=3.4, 10.5 Hz, 1H), 7.27-7.55 (m, 10H), 8.23 (d, J=2.7 Hz, 1H), 8.55 (d, J=2.7 Hz, 1H). Anal. Calcd for C22H22N2O·2.4 HCl·0.5 H2O: C, 61.89; H, 6.00; N, 6.56. Found: C, 62.04; H, 6.17; N, 6.03. [α]25D =-2.36° (c 1.95, MeOH).

Workup

  1. customThe solvent was removed under vacuum at 50° C.
  2. customthe residue was triturated with ether
  3. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-a2462a950e8e4d489bbd85293fd621fc
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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