Triethylamine → HCID 69059566, compound

HRID 731293Notes

Reaction equation

HRID 731293 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(CC)CC)C.[CH3:21][C:22]([CH3:27])([CH3:26])[CH2:23][CH:24]=O.C([BH3-])#N.[Na+]>CO>[CH2:12]([O:11][C:9]([C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:3]1[NH:2][CH2:24][CH2:23][C:22]([CH3:27])([CH3:26])[CH3:21])=[O:10])[CH3:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 763353,3-DimethylbutanalHCID 2724641ethyl (1R,2S)-2-aminocyclohexane-1-carboxylate hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 69059566HCID 69059566, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl cis-2-amino-1-cyclohexanecarboxylate hydrochloride (1.00 g, 4.6 mmol) in methanol (10 mL) was added triethylamine (0.72 mL, 5.1 mmol), 3,3-dimethylbutyraldehyde (0.67 mL, 5.1 mmol), and sodium cyanoborohydride (213.0 mg, 3.2 mmol) at 25° C. After stirring for 18 h, the mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude material was purified by flash column chromatography (Teledyne Isco RediSep Flash Column; 0-50% ethyl acetate in hexanes) to afford the desired product, cis-2-(3,3-dimethylbutylamino)-cyclohexanecarboxylic acid ethyl ester (31.2 mg, 0.061 mmol, 25%), as a white solid. 1H NMR (400 MHz, CDCl3) δ 0.99 (9H, s), 1.22-1.29 (1H, m), 1.35 (3H, t, J=7.0 Hz), 1.40-1.51 (1H, m), 1.58-1.77 (5H, m), 1.90-1.94 (1H, m), 2.12-2.15 (1H, m), 2.37-2.40 (1H, m), 2.96 (1H, bs), 3.09 (1H, bs), 3.22-3.33 (2H, m), 4.21-4.35 (2H, m). LC-MS (ESI) calcd for C15H29NO2 255.22, found 256.3 [M+H+].

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography (Teledyne Isco RediSep Flash Column; 0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-aa5157fc64fd48bd8002fa1a7448347e
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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