Piperidin-4-ol → 2-Trimethylsilanylethyl 4-hydroxypiperidine-1-carboxylate

HRID 1743258Notes

Reaction equation

HRID 1743258 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8](=O)([O:16]C1C=CC([N+]([O-])=O)=CC=1)[O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13].C(N(CC)C(C)C)(C)C>C1COCC1>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[O:16])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 30861164-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate

Product 1

HCID 222383902-Trimethylsilanylethyl 4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.9 g of 4-hydroxypiperidine were dissolved in 150 ml of THF. 19.4 g of 2-(trimethylsilyl)ethyl 4-nitrophenyl carbonate and 11.9 ml of N,N-diisopropylethylamine were successively added thereto. The mixture was stirred at room temperature for 1 h and then the solvent was removed in vacuo. The residue was taken up in 400 ml of ethyl acetate and washed once with 200 ml of 0.5 N HCl and twice with 200 ml of 1 N NaOH each time. The organic phase was dried with MgSO4, the solvent was removed in vacuo, and the residue was purified by chromatography on silica gel.

Workup

  1. customthe solvent was removed in vacuo
  2. washwashed once with 200 ml of 0.5 N HCl and twice with 200 ml of 1 N NaOH each time
  3. dry with materialThe organic phase was dried with MgSO4
  4. customthe solvent was removed in vacuo
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-01bd3e3f40964508949827221499fd62
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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