Methanol → Tert-butyl 2-(1-tert-butylpiperidin-4-yl)hydrazinecarboxylate

HRID 1530656Notes

Reaction equation

[C:1]([N:5]1[CH2:10][CH2:9][C:8](=[N:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.CO.O>C1COCC1>[C:1]([N:5]1[CH2:6][CH2:7][CH:8]([NH:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of tert-butyl 2-(1-tert-butylpiperidin-4-ylidene)hydrazinecarboxylate (400 mg, 1.49 mmol) in THF (40 mL) was added DIBAl-H (15 mL, 15 mmol) under nitrogen atmosphere. The resulting mixture was stirred at 25° C. overnight. Methanol (5 mL) was added at −78° C. After being stirred at room temperature for 1 h, water (10 mL) was added. The solid was filtered off and washed with EtOAc. The combined filtrate was partitioned and extracted with EtOAc (3×50 mL), dried over Na2SO4, and concentrated. The residue was purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:10) to give tert-butyl 2-(1-tert-butylpiperidin-4-yl)hydrazinecarboxylate (350 mg, 87% yield) as colorless oil. LCMS (ESI) m/z: 272.4 [M+H+].

Workup

stirringAfter being stirred at room temperature for 1 h
filtrationThe solid was filtered off
washwashed with EtOAc
customThe combined filtrate was partitioned
extractionextracted with EtOAc (3×50 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluting with EtOAc/petroleum ether (1:10)

Sources & evidence

ORD record: ord-97378d0d154a49d6a7a49f1a6e6d423f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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