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

HRID 736413
Notes
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Reaction equation

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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 115105321-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}cyclopentanecarboxylic acid

Product 1

HCID 67232469Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylateYield 67.2%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

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

  1. temperatureAfter cooling
  2. extractionextracted with AcOEt (200 mL) for three times
  3. washthe combined organic layer was washed with water (200 mL) and brine (200 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customRemoval of the solvent
  8. customgave a residue, which
  9. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes