1-(Tert-butoxycarbonyl)piperidine-3,5-dicarboxylic acid → Tert-butyl 2,4-dioxo-3-oxa-7-azabicyclo[3.3.1]nonane-7-carboxylate

HRID 1698362Notes

Reaction equation

HRID 1698362 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([C:14]([OH:16])=O)[CH2:11][CH:10]([C:17]([OH:19])=[O:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OC(=O)C)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH2:11][CH:12]([C:14](=[O:16])[O:19][C:17]2=[O:18])[CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 232911311-(Tert-butoxycarbonyl)piperidine-3,5-dicarboxylic acid

Product 1

HCID 59778297Tert-butyl 2,4-dioxo-3-oxa-7-azabicyclo[3.3.1]nonane-7-carboxylate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of piperidine-1,3,5-tricarboxylic acid 1-tert-butyl ester (1 g, 3.6 mmol) in acetic anhydride (20 mL) is heated at reflux for 2 h. The reaction mixture is evaporated 3× times with toluene before it is dried under high vacuum at rt overnight to give a yellow solid. MS (LC-MS): 278 [M+Na]+.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 h
  3. customThe reaction mixture is evaporated 3× times with toluene before it
  4. customis dried under high vacuum at rt overnight
  5. customto give a yellow solid

Sources & evidence

ORD record
ord-bde663a5bfbe42d6a5ca4c987091a082
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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