Lithium Hydroxide → HCID 86636609, compound

HRID 2381619Notes

Reaction equation

HRID 2381619 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][N:18]=[C:17]([Cl:26])[N:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1>[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([C:21]([OH:23])=[O:22])=[CH:19][N:18]=[C:17]([Cl:26])[N:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86636610HCID 86636610, compound

Product 1

HCID 86636609HCID 86636609, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(4-((tert-butoxycarbonyl)methyl)piperidin-1-yl)-2-chloropyrimidine-5-carboxylate (368 mg, 0.923 mmol) in THF (5 mL), aq. 1M LiOH (2.20 mL, 2.20 mmol) was added. It was heated to reflux for 5 h. THF was removed in vacuo. After being acidified with HOAc (2 mL), the residue was purified by HPLC to give 4-(4-((tert-butoxycarbonyl)methyl)piperidin-1-yl)-2-chloropyrimidine-5-carboxylic acid (150 mg). MS 371.4 and 373.4 (M+H, Cl pattern).

Workup

  1. temperatureIt was heated
  2. temperatureto reflux for 5 h
  3. customTHF was removed in vacuo
  4. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-ed93bcc30e6444329e87e344527cb4a9
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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