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

HRID 1177723Notes

Reaction equation

HRID 1177723 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-fe35296189a14f8f8fea249ca55297fc
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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