Hydrochloric Acid → HCID 21105440, compound

HRID 1354766Notes

Reaction equation

HRID 1354766 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([N:15]3[CH:19]4[CH2:20][CH2:21][CH:16]3[CH2:17][CH2:18]4)[C:11]2=O)=[CH:6][CH:5]=1)([O-])=O.B.C1COCC1.Cl>C1COCC1.O>[CH:19]12[N:15]([CH:12]3[CH2:13][CH2:14][N:10]([C:7]4[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=4)[CH2:11]3)[CH:16]([CH2:21][CH2:20]1)[CH2:17][CH2:18]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 21105369HCID 21105369, compound

Product 1

HCID 21105440HCID 21105440, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Nitrophenyl)-3-(7-azabicyclo[2.2.1]hept-7-yl)pyrrolidin-2-one (0.25 g) in THF (10 ml) was mixed with borane-THF complex (1M in THF, 0.83 ml) and boiled under reflux for 3 hours. After the reaction was complete, the mixture was diluted with water and adjusted to pH 9-10 with hydrochloric acid (4N). Extraction in ethyl acetate, drying and concentration of the organic phase afforded a crude product that was hydrogenated by method B. This resulted in the product with the molecular weight of 257.38 (C16H23N3); MS (ESI): 258 (M+H+).

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionExtraction in ethyl acetate
  3. customdrying
  4. customconcentration of the organic phase afforded a crude product that
  5. customThis resulted in the product with the molecular weight of 257.38 (C16H23N3)

Sources & evidence

ORD record
ord-a1d8a99d1c5e44dcb21b5d3345edd26c
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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