Triethylamine → Tert-butyl trans-4-(N-methoxy-N-methylcarbamoyl)cyclohexylcarbamate

HRID 899060

Reaction equation

HRID 899060 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].[CH3:18][O:19][NH:20][CH3:21].C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)CC)C>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][CH:12]([C:15](=[O:17])[N:20]([O:19][CH3:18])[CH3:21])[CH2:13][CH2:14]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 14232N,O-DimethylhydroxylamineHCID 27559964-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

Product 1

HCID 24720928Tert-butyl trans-4-(N-methoxy-N-methylcarbamoyl)cyclohexylcarbamateYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[N-(tert-butoxycarbonyl)amino]-cyclohexane carboxylic acid (11.95 g, 49.0 mmol), O,N-dimethylhydroxylamine (4.88 g, 50.0 mmol), DCC (9.60 g, 50 mmol) and triethylamine (5.06 g, 50.0 mmol) in DMF (150 mL) was stirred at room temperature overnight. Water (500 mL) was added and the mixture was extracted with CHCl3. The organic phase was washed with water, dried and concentrated under reduced pressure. Purification by flash chromatography (hexane/EtOAc 1:1) gave [4-(methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester (8.50 g, 61%).

Workup

  1. extractionthe mixture was extracted with CHCl3
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-04a1777065d14d92a4cdde19c8fed3d1
Source dataset
uspto-grants-2008_04
Patent number
US07354895B1

Linked notes

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