Piperidin-4-ol → 2-(Di-tert-butoxycarbonylamino)-3-(4-hydroxy-piperidin-1-yl)-propionic acid methyl ester

HRID 2250201Notes

Reaction equation

HRID 2250201 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([N:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH2:5].[NH:22]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]1>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:21])[CH:4]([N:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][N:22]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 79341Piperidin-4-olHCID 10870342Methyl 2-(bis((tert-butoxy)carbonyl)amino)prop-2-enoate

Product 1

HCID 588645182-(Di-tert-butoxycarbonylamino)-3-(4-hydroxy-piperidin-1-yl)-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(di-tert-butoxycarbonylamino)-acrylic acid methyl ester (1.0 g, 3.0 mmol) in acetonitrile (10 mL) was added piperidin-4-ol (0.33 g, 1.1 equiv). A gentle stream of nitrogen was placed over the reaction while it stirred overnight. The crude oil which resulted was dissolved in ethyl acetate, washed with water, then brine, dried over magnesium sulfate, and concentrated to give 1.38 g (quant.) as an oil which was used without purification. Mass spec.: 403.42 (MH)+.

Workup

  1. customA gentle stream of nitrogen was placed over the reaction while it
  2. customThe crude oil which resulted
  3. washwashed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give 1.38 g (quant.) as an oil which
  7. customwas used without purification

Sources & evidence

ORD record
ord-cf1547d5582249978087e07a3c49121e
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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