Sodium Hydroxide → (3S,4S)-1-Boc-4-methyl-piperidine-3-carboxylic acid

HRID 931303Notes

Reaction equation

HRID 931303 reaction equation
[OH-].[Na+].[CH3:3][C@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C@H:5]1[C:17]([O:19]CC)=[O:18]>CO>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C@H:4]([CH3:3])[C@H:5]([C:17]([OH:19])=[O:18])[CH2:6]1)=[O:11])([CH3:14])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131735164cis-1-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

Product 1

HCID 86317483(3S,4S)-1-Boc-4-methyl-piperidine-3-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

An aqueous solution of sodium hydroxide (2N, 20 mL) was added to a solution of cis-1-tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate (2.5 g, 9.21 mmol) in methanol (20 mL) at 0° C. The reaction mixture was stirred at 0° C. for 2 h. The solvent was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous layer was acidified to pH 2 using aqueous hydrochloric acid (1N) and was extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford cis-1-(tert-butoxycarbonyl)-4-methylpiperidine-3-carboxylic acid (2.2 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ede4e7d96faf4eb1aeb1eb37ca53e5a8
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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