1-Piperidinecarboxaldehyde → Tert-butyl 4-formylpyridin-3-ylcarbamate

HRID 1713134Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:2]=1.[Li]C(C)(C)C.N1([CH:26]=[O:27])CCCCC1.[NH4+].[Cl-]>C1COCC1>[CH:26]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][C:3]=1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:27]

Participants

Conditions

Temperature: -20 °C

Procedure

At −78° C., to a solution of tert-butyl pyridin-3-ylcarbamate (2.98 g, 15.34 mmol) in THF (60 mL) is added t-BuLi (1.7 N, 21.65 mL, 36.8 mmol) dropwise while maintaining the internal temperature below −70° C. Then, the mixture is allowed to warm to −20° C. for 2 hr and piperidine-1-carbaldehyde (5.11 mL, 46.02 mmol) is added dropwise and the mixture is stirred at −20° C. to rt overnight. Saturated NH4Cl solution (30 mL) is added and the layers are separated. The aqueous layer is extracted with EtOAc (45 ml) and the combined extracts are dried and evaporated. The residue is purified by flash column with hexane/EtOAc (4:1) to give the title compound as a white solid. MS (M+1): 223.1.

Workup

temperaturewhile maintaining the internal temperature below −70° C
customthe layers are separated
extractionThe aqueous layer is extracted with EtOAc (45 ml)
customthe combined extracts are dried
customevaporated
customThe residue is purified by flash column with hexane/EtOAc (4:1)

Sources & evidence

ORD record: ord-cf0019c884cc45d7a03ca8bc56017293
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795262B2

Reaction notes

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