Fumaric Acid → HCID 46829616, compound

HRID 907497Notes

Reaction equation

HRID 907497 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([NH2:18])[C:9]([CH3:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH3:10])[CH:5]=[CH:6][CH:7]=1.C(O)(=O)/C=C/C(O)=O>CCOC(C)=O.CO>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH2:18])[C:9]([CH3:10])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH3:17])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 46236227HCID 46236227, compound

Product 1

HCID 46829616HCID 46829616, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine is prepared is prepared starting from racemic 1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine using chiral SFC chromatography. The free base was dissolved in EtOAc and a solution of fumaric acid (1.0 eq) in MeOH is added. The solvent is removed in vacuo and the residue is triturated with Et2O/hexanes (1:1), collected by filtration and air-dried. 1HNMR (300 MHz, DMSO-d6) δ 1.19 (s, 3 H), 1.31 (s, 3 H), 4.48 (s, 1 H), 6.55 (s, 2 H), 6.85-6.95 (m, 2 H), 7.01 (t, J=8.9 Hz, 1 H), 7.18-7.34 (m, 3 H), 7.64-7.77 (m, 1 H), 8.59 (d, J=3.8 Hz, 1 H). MS: m/z 245.

Workup

  1. customis prepared
  2. customThe solvent is removed in vacuo
  3. customthe residue is triturated with Et2O/hexanes (1:1)
  4. filtrationcollected by filtration
  5. customair-dried

Sources & evidence

ORD record
ord-96a5fd8581dc4a7cb92232dd86db3df9
Source dataset
uspto-grants-2011_09
Patent number
US08013165B2

Reaction notes

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