Ammonium Chloride → 6-hydroxy-piperidine-1,2-dicarboxylic Acid 1-tert-butyl Ester 2-methyl Ester

HRID 722726Notes

Reaction equation

HRID 722726 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4].[NH4+].[Cl-]>C1COCC1>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([OH:11])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 108487371-(Tert-butyl) 2-methyl 6-oxopiperidine-1,2-dicarboxylate

Product 1

HCID 696595626-hydroxy-piperidine-1,2-dicarboxylic Acid 1-tert-butyl Ester 2-methyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester, 35, (5.1 g, 19.8 mmol) in THF (100 mL) at −78° C., a 1M solution of LiEt3BH in THF (22.0 mL, 22 mmol) is added. After stirring for 1 hr at −78° C., the solution is cautiously quenched aqueous NH4Cl. The crude product is extracted with EtOAc and the combined EtOAc extracts are washed with brine, dried (MgSO4), and concentrated in vacuo. The desired product is used without further purification.

Workup

  1. extractionThe crude product is extracted with EtOAc
  2. washthe combined EtOAc extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe desired product is used without further purification

Sources & evidence

ORD record
ord-2c8810679b9849d4aab81ab777d35f17
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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