Hydrochloric Acid → HCID 70009752, compound

HRID 1267905Notes

Reaction equation

HRID 1267905 reaction equation
[NH2:1][C@@H:2]1[CH2:8][CH2:7][C@@H:6]2[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C@@:3]1([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:4][CH2:5]2.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][C:26]=1[CH:27]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[ClH:52]>ClCCCl.C(O)(=O)C.C(OCC)(=O)C>[ClH:52].[ClH:52].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:30]([O:33][C:34]([F:35])([F:37])[F:36])=[CH:29][C:26]=1[CH2:27][NH:1][C@@H:2]1[CH2:8][CH2:7][C@@H:6]2[N:9]([CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@@:3]1([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:4][CH2:5]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70007021HCID 70007021, compound

Product 1

HCID 70009752HCID 70009752, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

(1R*,2R*,5S*)-2-amino-8-benzyl-1-phenyl-8-azabicyclo[3.2.1]octane (Description 9; 156 mg, 0.53 mmol) and 2-methoxy-5-(trifluoromethoxy)benzaldehyde (132 mg, 0.6 mmol) were dissolved in 1,2-dichloroethane (10 mL) and acetic acid (35 μL), and treated with sodium triacetoxyborohydride (127 mg, 0.6 mmol). The suspension formed was stirred at ambient temperature for 16 hours, then quenched with saturated aqueous sodium hydrogen carbonate solution (50mL). The mixture was extracted with dichloromethane (2×50 mL) and the extracts were dried (MgSO4), then concentrated. Purification of the residue gave the desired free base which was taken up in ethyl acetate (10 mL) and treated with ethereal hydrogen chloride (1M, 2 mL). The solid formed was recovered by filtration and recrystallized from methanol/diethyl ether to give the title compound as a white solid (178 mg, 0.3 mmol).

Workup

  1. customThe suspension formed
  2. customquenched with saturated aqueous sodium hydrogen carbonate solution (50mL)
  3. extractionThe mixture was extracted with dichloromethane (2×50 mL)
  4. dry with materialthe extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customPurification of the residue
  7. customgave the desired free base which
  8. customThe solid formed
  9. filtrationwas recovered by filtration
  10. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-61471ab53b7445cfb696ed55e3a2f057
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

Loading…