Water → HCID 86724914, compound

HRID 1523729Notes

Reaction equation

HRID 1523729 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)=[O:5])C.O1CCCC1.O.O.[OH-].[Li+]>C(OCC)(=O)C>[CH2:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)[CH2:13][CH2:14]1)=[O:19])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86724913HCID 86724913, compound

Product 1

HCID 86724914HCID 86724914, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of [1,4′]Bipiperidinyl-4,1′-dicarboxylic acid diethyl ester (5.51 grams, 17.67 mmol), tetrahydrofuran (34 mL) and water (34 mL) cooled at 0° C., lithium hydroxide monohydrate (742.0 mg, 17.67 mml) was added. The reaction mixture was stirred at room temperature for 16 hours, diluted with Ethyl acetate. The two layers were separated, the aqueous layer was acidified with 2N hydrochloric acid to pH: 3-4 and the volatiles were removed under reduced pressure to obtain [1,4′]Bipiperidinyl-4,1′-dicarboxylic acid 1′-ethyl ester (5.0 grams).

Workup

  1. customThe two layers were separated
  2. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-da1707567eb041e3b2f9de50ef4470bf
Source dataset
uspto-grants-2015_07
Patent number
US09079894B2

Reaction notes

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