Water → (S)-1-(tert-butoxycarbonyl)-6-oxopiperidine-3-carboxylic acid

HRID 58877Notes

Reaction equation

HRID 58877 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([OH:16])=[O:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH2:17]>CCOC(C)=O>[C:4]([O:3][C:1]([N:8]1[C:13](=[O:17])[CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 962WaterHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylate

Product 1

HCID 117690989(S)-1-(tert-butoxycarbonyl)-6-oxopiperidine-3-carboxylic acidYield 49%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of NaIO4 (5.6 g, 26 mmol) in water (30 mL) and RuCl3 (14 mg) were added to a solution of Boc-(R)-piperidine-3-carboxylic acid (1.5 g, 6.6 mmol) in EtOAc (30 mL). The reaction mixture was stirred overnight at ambient temperature. The two layers were separated and the aqueous phase was extracted with EtOAc (50 mL×3). The combined organic phases were washed with brine (50 mL×3), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (CH2Cl2/MeOH=20:1) to afford (S)-1-(tert-butoxycarbonyl)-6-oxopiperidine-3-carboxylic acid (790 mg, 49% yield) as a pale yellow solid.

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc (50 mL×3)
  3. washThe combined organic phases were washed with brine (50 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel (CH2Cl2/MeOH=20:1)

Sources & evidence

ORD record
ord-d9f44ceb39784ff4a5a8144d8d987207
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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