Triethylamine → Ethyl 1-(aminomethyl)spiro[2.5]octane-1-carboxylate

HRID 1796815Notes

Reaction equation

HRID 1796815 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:14]#[N:15])[C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C>C(O)C.[Ni]>[CH2:1]([O:3][C:4]([C:6]1([CH2:14][NH2:15])[C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 54753996Ethyl 1-cyanospiro[2.5]octane-1-carboxylate

Product 1

HCID 69599863Ethyl 1-(aminomethyl)spiro[2.5]octane-1-carboxylateYield 69.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-cyano-spiro[2.5]octane-1-carboxylic acid ethyl ester (7.1 g, 34.2 mmol) in 95 mL ethanol (EtOH) was added triethylamine (5.0 mL) and Raney nickel (4.0 g). The mixture was hydrogenated in a Parr shaker at 48 psi for 70 hours, filtered, and concentrated. Flash chromatography of the residue (5→10→15% MeOH/methylene chloride (CH2Cl2)) provided 5.0 g (69%) of 1-aminomethyl-spiro[2.5]octane-1-carboxylic acid ethyl ester as a colorless oil. 1H NMR δ 4.15 (q, J=7.1 Hz, 2H), 3.23 (d, J=13.9 Hz, 1H), 2.65 (d, J=13.9 Hz, 1H), 1.41–1.57 (m, 10H), 1.24 (m, 4H), 0.53 (d, J=4.9 Hz, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-df2dff56e2ad49b4aa390784d936aedc
Source dataset
uspto-grants-2006_04
Patent number
US07030267B2

Reaction notes

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