Dimethylamine → Tert-butyl{4-[(dimethylamino)carbonyl]cyclohexyl}carbamate

HRID 1946984Notes

Reaction equation

HRID 1946984 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[CH2:19][N:20]=[C:21]=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CNC>CN1C(=O)CCC1.CCOC(C)=O.O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15](=[O:17])[N:20]([CH3:21])[CH3:19])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27559964-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

Product 1

HCID 69309396Tert-butyl{4-[(dimethylamino)carbonyl]cyclohexyl}carbamateYield 59.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (2.43 g, 10 mmol), EDCI (6.52 g, 34 mmol) and HOBt (4.59 g, 34 mmol) in NMP (20 mL) was stirred at RT for 3 h. A solution of dimethylamine (2.0 M in THF, 15 mL, 30 mmol) was added, and the resulting mixture was stirred at RT for 64 h. Water and EtOAc were then added, and the organic layer was separated and washed twice with a saturated aqueous solution of K2CO3, aqueous HCl (1 M), a saturated aqueous solution of K2CO3, and brine. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure to give (4-dimethylcarbamoyl-cyclohexyl)-carbamic acid tert-butyl ester (1.6 g, 59% yield) as a white solid.

Workup

  1. stirringthe resulting mixture was stirred at RT for 64 h
  2. customthe organic layer was separated
  3. washwashed twice with a saturated aqueous solution of K2CO3, aqueous HCl (1 M)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b8df9fe13f734fa8af682b60dd5d4b46
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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