Piperidine → HCID 86655585, compound

HRID 39287Notes

Reaction equation

HRID 39287 reaction equation
[CH2:1]([P:4]([CH:9]([P:34]([CH2:39][CH:40]=[CH2:41])([CH2:36][CH:37]=[CH2:38])=[O:35])[NH:10][C:11](=[O:33])[NH:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC1C2C=CC=CC=2C2C1=CC=CC=2)=[O:17])([CH2:6][CH:7]=[CH2:8])=[O:5])[CH:2]=[CH2:3].N1CCCCC1>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH2:1]([P:4]([CH:9]([P:34]([CH2:36][CH:37]=[CH2:38])([CH2:39][CH:40]=[CH2:41])=[O:35])[NH:10][C:11](=[O:33])[NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])([CH2:6][CH:7]=[CH2:8])=[O:5])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 86655586(9H-Fluoren-9-yl)methyl 4-(3-(bis(diallylphosphoryl)methyl)ureido)butanoate

Product 1

HCID 86655585HCID 86655585, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Ester 152 (778 mg, 1.18 mmol) was treated with a 5% v/v solution of piperidine in DMF (6 mL). After stirring for 50 min, the reaction mixture was diluted with saturated NaHCO3 solution and washed once with Et2O. The aqueous layer was acidified to pH 2 with conc. HCl solution and extracted with a 4:1 mixture of CHCl3/i-PrOH (3×). The organic layers were combined, dried over MgSO4, filtered and concentrated to dryness, yielding acid 153 as yellowish oil (520 mg, 92%) which was used without purification. 1H NMR (400 MHz, CDCl3) δ 1.84 (quint, J=6.4 Hz, 2H), 2.35 (t, J=6.6 Hz, 2H), 3.26-3.29 (m, 2H), 4.52-4.67 (m, 8H), 5.04 (dt, J=22.2, 10.1 Hz, 1H), 5.20-5.27 (m, 4H), 5.30-5.40 (m, 4H), 5.751 (bs, 1H), 5.84-5.98 (m, 4H), 6.90 (d, J=10.3 Hz, 1H).

Workup

  1. washwashed once with Et2O
  2. extractionextracted with a 4:1 mixture of CHCl3/i-PrOH (3×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e1c26ff0625d45e883258c7867876da5
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Reaction notes

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