Methanol → HCID 86700542, compound

HRID 2203136Notes

Reaction equation

HRID 2203136 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[C:8](=O)[N:7]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:5].CO>C1COCC1>[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8][N:7]1[C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[O:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 86700543HCID 86700543, compound

Product 1

HCID 86700542HCID 86700542, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-5-methyl-6-oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (10 g, 35 mmol) in THF (150 mL) was added borane dimethylsulfide complex (49 mL, 49 mmol). The reaction mixture was stirred at 0° C. for 1 h, and then stirred at 40° C. for 3 h. Methanol was added and the reaction mixture was concentrated, washed with 1 M HCl, and extracted with EtOAc/water to give the oil layer, which was dried, and concentrated. The crude product was purified by silica gel chromatography (20:1 petroleum ether:EtOAc) to provide the title intermediate (2 g, 21% yield). (m/z): [M−100+H]+ calcd for C14H25NO4 172.18 found 172.2.

Workup

  1. stirringstirred at 40° C. for 3 h
  2. concentrationthe reaction mixture was concentrated
  3. washwashed with 1 M HCl
  4. extractionextracted with EtOAc/water
  5. customto give the oil layer, which
  6. customwas dried
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (20:1 petroleum ether:EtOAc)

Sources & evidence

ORD record
ord-8334883e99ae4541973b270d41bb4c9b
Source dataset
uspto-grants-2016_06
Patent number
US09365549B2

Reaction notes

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