Aluminium lithium hydride → 1-Boc-piperidine-3-carboxaldehyde

HRID 2115660Notes

Reaction equation

HRID 2115660 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([C:20](N(OC)C)=[O:21])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C(OCC)C.C1COCC1>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH:20]=[O:21])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22248320Tert-butyl 3-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate

Product 1

HCID 99644481-Boc-piperidine-3-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

To a cooled (−15° C.), stirred suspension of lithium aluminum hydride (4.355 g, 114.743 mmol) in diethyl ether (500 mL) was added dropwise a solution of 3-{[methoxy(methyl)amino]carbonyl}-1-piperidine-carboxylic acid tert-butyl ester (25.000 g, 91.795 mmol) in THF (150 mL) over 30 min. The reaction mixture was quenched with aqueous 1N potassium hydrogen sulfate (300 mL), and extracted with a 1:1 mixture of diethyl ether and ethyl acetate. The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure to give 3-formylpiperidine-1-carboxylic acid tert-butyl ester, which was used for the next steps without further purification. (22.56 g, yield; quant.)

Workup

  1. customThe reaction mixture was quenched with aqueous 1N potassium hydrogen sulfate (300 mL)
  2. extractionextracted with a 1:1 mixture of diethyl ether and ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-771a3d4271c742b2b49fcba4f22bb498
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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