Diisopropylethylamine → Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate

HRID 736413

Reaction equation

C(N1C2C=CC=CC=2N([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:19][CH2:18]2)=[O:14])C1=O)(C)C.N1CCC(CNC(=O)[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])CC1.[CH3:48]CN(C(C)C)C(C)C>CN1CCCC1=O.C([O-])(O)=O.[Na+]>[C:43]([O:42][C:13]([NH:15][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([CH2:23][C:24]2([C:29]([O:31][CH3:48])=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:21][CH2:22]1)=[O:14])([CH3:46])([CH3:45])[CH3:44]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of Methyl 1-(iodomethyl)cyclopentanecarboxylate (5.52 g, 0.0206 mol, Step 1), tert-butyl (piperidin-4-ylmethyl)carbamate (8.83 g, 0.0412 mol) and iPr2NEt (10.76 mL, 0.0618 mol) in N-methylpyrrolidone (70 mL) was stirred at 120° C. for 24 h. After cooling, the reaction mixture was diluted with sat. NaHCO3 aq. (200 mL), extracted with AcOEt (200 mL) for three times, and the combined organic layer was washed with water (200 mL) and brine (200 mL). The organic layer was dried over Na2SO4, filtered and concentrated. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1) to give 4.91 g (67%) of title compound as a yellow syrup.

Workup

temperatureAfter cooling
extractionextracted with AcOEt (200 mL) for three times
washthe combined organic layer was washed with water (200 mL) and brine (200 mL)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customRemoval of the solvent
customgave a residue, which
customwas chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1)

Sources & evidence

ORD record: ord-df2cbae2cf924e569589faf7c96324f7
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595329B2

Linked notes

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