Hydrochloric Acid → HCID 86610911, compound

HRID 2377034Notes

Reaction equation

HRID 2377034 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:20]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[ClH:37]>CCOC(C)=O>[ClH:37].[F:36][C:2]([F:1])([F:35])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:20]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[CH2:19][NH:18][CH2:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86610907HCID 86610907, compound

Product 1

HCID 86610911HCID 86610911, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1.5 g (2.876 mmol) tert-butyl (3R,4S)-3-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}oxy)-4-(4-fluorophenyl)pyrrolidine-1-carboxylate (Step C) in 10 mL EtOAc was added 10 mL of a solution of sat. anhdr. HCl in EtOAc. The reaction mixture was a stirred at RT for 24 hr and the solvent removed under vacuum to afford a yellow oil. The resulting oil was recrystallized from ether/hexanes (3/7) to afford the title compound as a white solid (mp=107° C.). 1H-NMR (CD3OD): δ: 1.43 (d, 3H, 6.5 Hz), 3.27 (t, 1H, 8.5 Hz), 3.44 (m, 2H), 3.73 (m, 2H), 4.20 (q, 1H, 5.5 Hz), 4.78 (q, 1H, 6.5 Hz), 7.01 (t, 2H), 7.20 (dd, 2H), 7.73 (s, 2H), 7.82 (s, 1H)ppm. MS: 422.1 (MH)+ observed.

Workup

  1. customthe solvent removed under vacuum
  2. customto afford a yellow oil
  3. customThe resulting oil was recrystallized from ether/hexanes (3/7)

Sources & evidence

ORD record
ord-84966625c8ba43478c352468eeed1152
Source dataset
uspto-grants-2008_12
Patent number
US07468437B2

Reaction notes

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