Diethylamine → (1-Diethylcarbamoylmethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester

HRID 1713029Notes

Reaction equation

HRID 1713029 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([CH2:16][C:17]([OH:19])=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[CH2:32]([N:34](CC)[CH2:35][CH3:36])[CH3:33].C(NCC)C.C(OC(N1C(=O)CC2(CCCCC2)C1)=O)(C)(C)C>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.C(Cl)(Cl)Cl.CCCCCC>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1([CH2:16][C:17](=[O:19])[N:34]([CH2:35][CH3:36])[CH2:32][CH3:33])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)([CH3:2])([CH3:3])[CH3:4]

Participants

11

Reactant 5

HCID 8021DiethylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559412-(1-((((Tert-butoxy)carbonyl)amino)methyl)cyclohexyl)acetic acidHCID 685035643-Oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester

Product 1

HCID 68502511(1-Diethylcarbamoylmethyl-cyclohexylmethyl)-carbamic acid tert-butyl esterYield 76%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

[1-(Tert-butoxycarbonylamino-methyl)-cyclohexyl]-acetic acid (271 mg, 1 mmol) was dissolved in dry dichloromethane (5 ml) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC-HCl; 576 mg, 3 mmol, 3 molequivalents) and triethylamine (404 mg, 4 mmol, 4 molequivalents) were added thereto. After 10 minutes of stirring, diethylamine (146 mg, 2 mmol, 2 molequivalents) and 4-dimethylamino-pyridine (DMAP; 25 mg, 0.2 mmol, 0.2 molequivalents) were added to the reaction mixture, and the mixture was stirred at 25° C. for 20 hours, while monitoring the reaction by TLC using a 2:8 hexane:ethyl acetate mixture as eluent, and until the appearance of a spot of the amide in the middle of the TLC plate was observed. Chloroform was thereafter added and the mixture was washed with NaHCO3, twice with 1M HCl, dried over Na2SO4 and the solvents were evaporated under reduced pressure to give (1-diethylcarbamoylmethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (248 mg, 76% yield) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at 25° C. for 20 hours
  2. customthe reaction by TLC
  3. washthe mixture was washed with NaHCO3, twice with 1M HCl
  4. dry with materialdried over Na2SO4
  5. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-30d34214ce804d99b23a091d0811df36
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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