1H-1,2,4-Triazole → HCID 19969700, compound

HRID 1592742Notes

Reaction equation

HRID 1592742 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20]O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:22]1[CH:26]=[N:25][CH:24]=[N:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][N:22]2[CH:26]=[N:25][CH:24]=[N:23]2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 7127802tert-Butyl 4-[2-(hydroxymethyl)phenyl]piperazine-1-carboxylate

Product 1

HCID 19969700HCID 19969700, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-Boc-4-(hydroxymethyl-phenyl)-piperazine (300 mg, 1.02 mmol, 1.0 eq.), 1,2,4 triazole (104 mg, 1.53 mmol, 1.5 eq.), triphenylphosphine (535 mg, 2.04 mmol, 2.0 eq.) and THF at 0° C. under nitrogen was added DEAD (0.321 mL, 2.04 mmol, 2.0 eq.) slowly so that temperature of reaction does not rise above 10° C. After addition was completed, the ice bath was removed and the reaction mixture was stirred at r.t. overnight. Methanol was added and the mixture was stirred for about 15 minutes. The mixture was then concentrated. Purification by flash chromatography (35 g SiO2, linear gradient 50-70% EtOAc/Hexane for 15 minutes and 70% EtOAc for 18 minutes) afforded Boc protected title compound (200 mg, 0.5 mmol, 57%). LRMS (ESI+): 344.1 (M+1)

Workup

  1. customslowly so that temperature of reaction
  2. customdoes not rise above 10° C
  3. additionAfter addition
  4. customthe ice bath was removed
  5. additionMethanol was added
  6. stirringthe mixture was stirred for about 15 minutes
  7. concentrationThe mixture was then concentrated
  8. customPurification by flash chromatography (35 g SiO2, linear gradient 50-70% EtOAc/Hexane for 15 minutes and 70% EtOAc for 18 minutes)
  9. customafforded Boc

Sources & evidence

ORD record
ord-f503c811be95421ab3e784002dfe2509
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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