Borane;tetrahydrofuran → HCID 25265632, compound

HRID 2194840Notes

Reaction equation

HRID 2194840 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:10][CH2:11][CH:12]2[CH2:16][N:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:14](=O)[CH2:13]2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[CH2:16]2)[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 25265629HCID 25265629, compound

Product 1

HCID 25265632HCID 25265632, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 100 mL round-bottomed flask was charged with 4-({[(1R)-1-(3-chlorophenyl)ethyl]amino}methyl)-1-(4-fluorophenyl)pyrrolidin-2-one 56 (0.400 g, 1.0 mmol) as a 1:1 mixture of diastereomers and 10 mL of THF. To this solution was added BH3.THF (1 M in THF, 5.2 mL, 5.2 mmol). The mixture was heated to reflux for 3 h then cooled to 0° C. The reaction was quenched with saturated aqueous NaHCO3 and extracted with CH2Cl2. The extracts were dried and concentrated to give an oil, which was purified by column chromatography on silica gel (2% to 7% MeOH in DCM) to give (1R)-1-(3-chlorophenyl)-N-{[1-(4-fluorophenyl)pyrrolidin-3-yl]methyl}ethanamine 58 as a 1:1 mixture of diastereomers. Mass spectrum, calculated for C19H22ClFN2 332.1; found 333.2 (M++1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. customThe reaction was quenched with saturated aqueous NaHCO3
  4. extractionextracted with CH2Cl2
  5. customThe extracts were dried
  6. concentrationconcentrated
  7. customto give an oil, which
  8. customwas purified by column chromatography on silica gel (2% to 7% MeOH in DCM)

Sources & evidence

ORD record
ord-5e69e6a2100f45e38a602e1ee52b90ff
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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