1-Aminocyclohexanecarboxylic acid → Methyl 1-aminocyclohexanoate

In a round-bottomed flask 1-amino-1-cyclohexanecarboxylic acid (1.00 g, 7.0 mmol) was suspended in dichloromethane (26 mL) and MeOH (13 mL). (Trimethylsilyl)diazomethane (2.0 M in hexanes, 6.0 mL, 12.0 mmol) was added dropwise and the reaction mixture gradually became homogeneous as it was stirred at room temperature overnight. The reaction mixture was quenched with a small portion of acetic acid and concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with saturated aqueous Na2CO3. The aqueous layer was extracted with dichloromethane and the combined organics were dried over Na2SO4 and concentrated to afford 1.15 g of 1-amino-1-cyclohexanecarboxylic acid methyl ester as a light yellow oil.

1. customThe reaction mixture was quenched with a small portion of acetic acid
2. concentrationconcentrated under reduced pressure
3. dissolutionThe residue was dissolved in dichloromethane
4. washwashed with saturated aqueous Na2CO3
5. extractionThe aqueous layer was extracted with dichloromethane
6. dry with materialthe combined organics were dried over Na2SO4
7. concentrationconcentrated

ORD record

ord-97b1579893f14b25ac678687f3c11913

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329699B2