Methyl 2-oxocycloheptane-1-carboxylate → 2-(N'-allyl-N'-cyclobutyl-hydrazino)-cycloheptanecarboxylic acid methyl ester

HRID 731389Notes

Reaction equation

Cl.[CH2:2]([N:5]([CH:7]1[CH2:10][CH2:9][CH2:8]1)[NH2:6])[CH:3]=[CH2:4].[CH3:11][O:12][C:13]([CH:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=O)=[O:14].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>CO>[CH3:11][O:12][C:13]([CH:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[NH:6][N:5]([CH2:2][CH:3]=[CH2:4])[CH:7]1[CH2:10][CH2:9][CH2:8]1)=[O:14]

Participants

Conditions

Temperature: 25 °C

Procedure

N′-Allyl-N′-cyclobutyl-hydrazine hydrochloride (2.01 g, 12.37 mmol) was dissolved in methanol (40 mL). 2-Oxo-cycloheptanecarboxylic acid methyl ester (1.93 mL, 12.37 mmol), sodium acetate (2.04 g, 24.74 mmol), sodium cyanoborohydride (1.55 g, 24.74 mmol) and 4 Å molecular sieves (2.80 g) were added sequentially. The reaction was stirred at 25° C. for 18 h before it was quenched via the addition of saturated aqueous sodium bicarbonate solution (30 mL). The mixture was extracted with ethyl acetate (3×40 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to afford the crude product, 2-(N′-allyl-N′-cyclobutyl-hydrazino)-cycloheptanecarboxylic acid methyl ester, as a yellow oil. The residue was used directly in the next step. LC-MS (ESI) calcd for C16H28N2O2 280.41, found 281.2 [M+H+].

Workup

customwas quenched via the addition of saturated aqueous sodium bicarbonate solution (30 mL)
extractionThe mixture was extracted with ethyl acetate (3×40 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4db1f50953f945efb13a2e9ae5374d58
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582626B2

Reaction notes

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