tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate → tert-Butyl 4-formylpiperidine-1-carboxylate

HRID 1038037Notes

Reaction equation

HRID 1038037 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20](=[O:25])N(OC)C)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CCOCC>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([CH:20]=[O:25])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of lithium aluminum hydride (1M THF solution, 4.4 ml) in ether (4 ml) was added dropwise at −60 C4-(methoxy-methyl-carbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (1 g, 3.67 mmols) in ether (6 ml). The reaction mixture was allowed to warm to 0-5 C and then re-cooled to −60 C. Celite was added and reaction was quenched with a solution of KHSO4 (19) in water (3 ml), filtered through Celite. The filtrate was washed with cold 1N HCl, saturated NaHCO3, brine and dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel eluting with ethyl acetate in hexanes (1:1) to provide title compound (656 mg, 84%). (Org. Prep. Proced. Int., 2000, 32, 96.)

Workup

  1. temperatureto warm to 0-5 C
  2. temperaturere-cooled to −60 C
  3. additionCelite was added
  4. customreaction
  5. customwas quenched with a solution of KHSO4 (19) in water (3 ml)
  6. filtrationfiltered through Celite
  7. washThe filtrate was washed with cold 1N HCl, saturated NaHCO3, brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate in hexanes (1:1)

Sources & evidence

ORD record
ord-e192f916f49c49bca19f60b1dc246cba
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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