Ammonium Chloride → HCID 58415264, compound

HRID 2075232Notes

Reaction equation

HRID 2075232 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]4[CH2:27][CH:26]([C:28]([O:30][CH3:31])=[O:29])[CH2:25]4)=[CH:19][C:18]=3[F:32])=[CH:14][C:13]=2[CH:33]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.C1COCC1>[F:32][C:18]1[CH:19]=[C:20]([CH2:23][N:24]2[CH2:25][CH:26]([C:28]([O:30][CH3:31])=[O:29])[CH2:27]2)[CH:21]=[CH:22][C:17]=1[C:15]1[O:16][C:12]2[CH:11]=[CH:10][C:9]([CH:1]([OH:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:33][C:13]=2[CH:14]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 58415397HCID 58415397, compound

Product 1

HCID 58415264HCID 58415264, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To solution of methyl 1-((4-(5-benzoylbenzofuran-2-yl)-3-fluorophenyl)methyl)-azetidine-3-carboxylate (190 mg, 428 μmol) in MeOH (5.0 mL; 0.14M) and THF (1.0 mL) was added sodium borohydride (130 mg, 3438 μmol) at 0° C., and the resulting mixture was stirred at 0° C. for 10 min, then at 25° C. for 30 min. Saturated aqueous ammonium chloride (10 mL) was added, and the resulting mixture was extracted twice with EtOAc (30 mL). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (ISCO, 4 g, 0-100% EtOAc/hexanes) furnished (±)-methyl 1-((3-fluoro-4-(5-(hydroxy(phenyl)methyl)benzofuran-2-yl)phenyl)methyl)azetidine-3-carboxylate as a clear oil. MS (ESI) m/z: Calculated: 445.2; Observed: 446 (M++1).

Workup

  1. waitat 25° C. for 30 min
  2. extractionthe resulting mixture was extracted twice with EtOAc (30 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification of the residue (ISCO, 4 g, 0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8906de8f1eb24b7b86eb759cb4e064b6
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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