Phosphorus oxychloride → HCID 60108780, compound

HRID 1005657Notes

Reaction equation

HRID 1005657 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[CH:19]3)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 60108792HCID 60108792, compound

Product 1

HCID 60108780HCID 60108780, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-hydroxy-4-(1H-indol-7-yl)-piperidine-1-carboxylic acid tert-butyl ester (117 mg, 0.37 mmol) in pyridine (5 mL) was added POCl3 (70 μL, 0.74 mmol) in a single portion. The reaction was stirred for 24 h, quenched with the slow addition of water (10 mL) and extracted with EtOAc (3×10 mL). The combined acetate layers were washed with brine, dried (MgSO4) and concentrated to afford 4-(1H-indol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a light yellow oil (100 mg).

Workup

  1. customquenched with the slow addition of water (10 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined acetate layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-394a608a227a414dbe35a9b3128850ad
Source dataset
uspto-grants-2004_09
Patent number
US06787535B2

Reaction notes

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