Water → (1S,4R)-4-phenylcyclopent-2-enamine

HRID 2404377Notes

Reaction equation

HRID 2404377 reaction equation
[N:1]([C@H:4]1[CH2:8][C@@H:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5]1)=[N+]=[N-].CC1CCCO1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(OC)(C)C>[C:9]1([C@@H:7]2[CH2:8][C@H:4]([NH2:1])[CH:5]=[CH:6]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73012-MethyltetrahydrofuranHCID 11776TriphenylphosphineHCID 130951056((1R,4S)-4-azidocyclopent-2-enyl)benzene

Product 1

HCID 68313332(1S,4R)-4-phenylcyclopent-2-enamine

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of Example 48B (530 mg, 2.86 mmol), 2-methyl tetrahydrofuran (9.5 mL), water (1.056 mL), and triphenylphosphine (900 mg, 3.43 mmol) was heated to 70° C. After 50 minutes, LCMS showed complete reaction. The mixture was diluted with MTBE (50 mL) and extracted with 2N HCl (25 mL) and water (25 mL). Aqueous 2N NaOH (30 mL) was added to the aqueous layer, followed by extraction with MTBE (50 mL×3). The final organic layers were dried (Na2SO4), filtered, and concentrated to provide the title compound, which was used crude in the next step. MS (DCI) m/z 160 (M+H)+.

Workup

  1. customreaction
  2. extractionextracted with 2N HCl (25 mL) and water (25 mL)
  3. additionAqueous 2N NaOH (30 mL) was added to the aqueous layer
  4. extractionfollowed by extraction with MTBE (50 mL×3)
  5. dry with materialThe final organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9734ef036b0445b8a63163a8b6534617
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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