Triethylamine → (1R,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexanecarboxylic acid

HRID 2222921Notes

Reaction equation

HRID 2222921 reaction equation
[C@@H:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.Cl.[NH2:13][CH2:14][C:15]#[N:16].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.O1CCCC1>[C:14]([CH2:15][NH:16][C:7]([C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:1]1[C:10]([OH:9])=[O:11])=[O:8])#[N:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11491918Aminoacetonitrile hydrochlorideHCID 12261141(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride

Product 1

HCID 11622584(1R,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(+)-trans-Cyclohexane-1,2-dicarboxylic anhydride (100 mg, 0.65 mmol) was weighed into a 10 mL round bottom flask and aminoacetonitrile hydrochloride (135 mg, 1.46 mmol) and 4-(dimethylamino)pyridine (7.5 mg, 61 μmol) added. After adding tetrahydrofuran (2.0 mL) and triethylamine (0.20 mL, 1.4 mmol), the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was partitioned between 1 M aqueous hydrochloric acid (30 mL) and ethyl acetate (30 mL). The organic layer was separated, washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated to give (1R,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexanecarboxylic acid (as a colorless solid.

Workup

  1. customThe reaction mixture was partitioned between 1 M aqueous hydrochloric acid (30 mL) and ethyl acetate (30 mL)
  2. customThe organic layer was separated
  3. washwashed with saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8a19fea8900043108417ce7865c1f8c1
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

Loading…