Hydrochloric Acid → HCID 69000071, compound

HRID 1909647Notes

Reaction equation

HRID 1909647 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.[ClH:27]>O1CCOCC1>[ClH:27].[CH2:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C@@H:7]2[CH2:8][CH2:9][CH2:10][N:6]2[CH2:5][CH2:4][C:3]([OH:26])=[O:2])=[CH:14][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68999410HCID 68999410, compound

Product 1

HCID 69000071HCID 69000071, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-[(S)-2-(4-Benzyl-phenoxymethyl)-pyrrolidin-1-yl]-propionic acid methyl ester (32.6 mg, 0.092 mmol) was added to a solution of HCl (conc.) in Dioxane (1:3, 2 mL). The reaction was run a 60° C. for 4 h. The Mixture was concentrated to dryness and dried in a vacuum over at 50° C. The residue was triturated with diethyl ether and dried to provide the title product (19 mg, 0.056 mmol, 60% yield); LCMS: m/z 339.44 (free amine), found 340 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 1.77 1.837 (m, 1H), 1.93-1.96 (m, 1H), 1.99-2.04 (m, 1H), 2.20-2.25 (m, 1H), 2.80-2.85 (m, 1H), 3.16-3.18 (m, 1H), 3.31-3.41 (m, 1H), 3.56-3.88 (m, 6H), 4.25-4.32 (m, 2H), 6.90-6.92 (d, J=8.4, 2H), 7.16-7.21 (m, 5H), 7.26-7.29 (m, 2H), 10.34 (s, 1H).

Workup

  1. concentrationThe Mixture was concentrated to dryness
  2. customdried in a vacuum over at 50° C
  3. customThe residue was triturated with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-2942bdd6bbec47d38283af589a4a31df
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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