Ethyl chloroformate → HCID 62358690, compound

HRID 2249885Notes

Reaction equation

HRID 2249885 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[OH:8].[CH2:9]([O:11][C:12](Cl)=[O:13])[CH3:10].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:9]([O:11][C:12](=[O:13])[NH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[OH:8])[CH3:10]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 232862-Aminocyclohexanol

Product 1

HCID 62358690HCID 62358690, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-cyclohexanol (3.50 g 23.0 mmol, 1.0 eq.) in CH2Cl2 (100 mL) was added ethylchloroformate (2.65 mL, 1.2 eq.) followed by an aqueous solution of K2CO3 (16.0 g in 200 mL of H2O). The mixture was stirred vigorously for 1 h. The separated aqueous layer was extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and concentrated to give (2-hydroxy-cyclohexyl)-carbamic acid ethyl ester (4.36 g, >100%).

Workup

  1. extractionThe separated aqueous layer was extracted twice with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-60743a702ffb4e3f9a7c81e39a5b6abf
Source dataset
uspto-grants-2008_01
Patent number
US07314936B2

Reaction notes

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