Lithium Hydroxide → 1-(4-Nitro-benzenesulfonyl)-piperidine-4-carboxylic acid

HRID 1841954Notes

Reaction equation

HRID 1841954 reaction equation
[OH-].[Li+].C[O:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:9][CH2:8]1)=[O:6]>C1COCC1.O>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([S:13]([N:10]2[CH2:9][CH2:8][CH:7]([C:5]([OH:6])=[O:4])[CH2:12][CH2:11]2)(=[O:14])=[O:15])=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 3112496HCID 3112496, compound

Product 1

HCID 7378411-(4-Nitro-benzenesulfonyl)-piperidine-4-carboxylic acidYield 54%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (1.45 g, 60.9 mmol) was added in one portion to a stirred solution of 1-(4-nitro-benzenesulfonyl)-piperidine-4-carboxylic acid methyl ester (10.0 g, 30.4 mmol) in THF/H2O (1:1,100 ml) and the reaction mixture was stirred at room temperature for 2 hours. After this time, the reaction mixture was partitioned between ethyl acetate (100 ml) and HCl (2M, 20 ml), the organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum to afford the title compound (5.1 g, 54% yield) as a colourless oil. δH (250 MHz, DMSO) 12.33 (1H, br s), 8.42 (2H, d), 7.99 (2H, d), 3.56-3.44 (2H, m), 2.51 (2H, obscured), 2.32-2.20 (1H, m), 1.90-1.81 (2H, m), 1.62-1.45 (2H, m). Tr=1.71 min m/z (ES+) (M+H+) 315.

Workup

  1. customAfter this time, the reaction mixture was partitioned between ethyl acetate (100 ml) and HCl (2M, 20 ml)
  2. customthe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f52bd66f3e984555ab8aee77b7b7c673
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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