Diisopropylethylamine → 2-(Trimethylsilyl)ethyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1743265Notes

Reaction equation

HRID 1743265 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[C:9](=O)([O:17]C1C=CC([N+]([O-])=O)=CC=1)[O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14].C(N(CC)C(C)C)(C)C>C1COCC1>[OH:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([C:9]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:17])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4207714-PiperidinemethanolHCID 30861164-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate

Product 1

HCID 113689482-(Trimethylsilyl)ethyl 4-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.5 g of 4-piperidinylmethanol were dissolved in 170 ml of THF. 25.8 g of 2-(trimethylsilyl)ethyl 4-nitrophenyl carbonate and 15.9 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 300 ml of 0.5 N HCl and twice with 250 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 300 ml of 0.5 N HCl and twice with 250 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-e0f6906ac249442a966b213a3998dfcf
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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