Water → Benzyl 4-(aminomethyl)-4-fluoropiperidine-1-carboxylate

HRID 1351604Notes

Reaction equation

HRID 1351604 reaction equation
[N:1]([CH2:4][C:5]1([F:21])[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[NH2:1][CH2:4][C:5]1([F:21])[CH2:6][CH2:7][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 22135652Benzyl 4-(azidomethyl)-4-fluoropiperidine-1-carboxylate

Product 1

HCID 22135645Benzyl 4-(aminomethyl)-4-fluoropiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 4-(azidomethyl)-4-fluoropiperidine-1-carboxylate (1.5 g, 5.1 mmol) in THF (10 mL) at RT was added water (0.92 mL, 0.92 mmol) and triphenylphosphine (4.3 g, 15.4 mmol). The reaction mixture was stirred for 60 h, concentrated, dissolved in HCl (1M) and extracted with Et2O four times. The aqueous layer was basified to pH 11 and extracted with EtOAc twice. The organic layer was dried over Na2SO4, filtered and concentrated. The crude mixture was chromatographed on silica gel (CH2Cl2 to 80:20:2 CH2Cl2:MeOH:NH4OH) to give benzyl 4-(aminomethyl)-4-fluoropiperidine-1-carboxylate. M.S. (M+1): 267

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in HCl (1M)
  3. extractionextracted with Et2O four times
  4. extractionextracted with EtOAc twice
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude mixture was chromatographed on silica gel (CH2Cl2 to 80:20:2 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-b34b7a2b37d64350a34dc556b1dd1d48
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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