Pyridine → HCID 57671221, compound

HRID 731243Notes

Reaction equation

HRID 731243 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:5])[CH3:2].B.N1C=CC=CC=1>C(O)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6331BoraneHCID 57671183HCID 57671183, compound

Product 1

HCID 57671221HCID 57671221, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-[(pyridin-2-ylmethyl)-amino]-cyclopent-1-enecarboxylic acid ethyl ester (4.78 g, 19.4 mmol) in acetic acid (70 mL) was treated with a 8.0 M solution of borane in pyridine (2.67 mL, 21.4 mmol) and stirred under a nitrogen atmosphere for 30 min. The reaction was quenched with 1.0 M aqueous hydrochloric acid solution (40 mL) for 16 h. The reaction was then poured into a mixture of saturated aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL) and extracted. The organic layer was dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0-10% methanol in dichloromethane) to afford the desired product, 2-[(pyridin-2-ylmethyl)-amino]-cyclopentanecarboxylic acid ethyl ester (3.30 g, 13.3 mmol, 68.6%), as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) δ: 1.16 (3H, t, J=7.4 Hz), 1.38-1.79 (4H, m), 1.82-1.96 (2H, m), 2.56 (1H, dd, J1=15.5 Hz, J2=7.0 Hz), 2.88 (1H, dd, J1=14.9 Hz, J2=7.1 Hz), 3.21 (1H, dd, J1=13.7 Hz, J2=6.7 Hz), 4.04 (2H, q, J=7.0 Hz), 3.78 (2H, s), 7.19-7.22 (2H, m), 7.38 (1H, d, J=7.6 Hz), 7.68-7.73 (1H, m), 8.45 (1H, d, J=4.7 Hz). LC-MS (ESI) calcd for C14H20N2O2 248.15, found 249.2 [M+H+].

Workup

  1. customThe reaction was quenched with 1.0 M aqueous hydrochloric acid solution (40 mL) for 16 h
  2. additionThe reaction was then poured into a mixture of saturated aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL)
  3. extractionextracted
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-2a5f43ee473f4a19a50bb5d0f505aca1
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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