Benzyl succinimido carbonate → HCID 178484047, compound

HRID 967140Notes

Reaction equation

HRID 967140 reaction equation
[CH3:1][NH:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][OH:11])[CH2:6][CH2:5]1.[CH2:12]([O:19][C:20]([O:22]N1C(=O)CCC1=O)=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH2:12]([O:19][C:20](=[O:22])[N:2]([CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)[CH3:1])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 178484044HCID 178484044, compound

Product 1

HCID 178484047HCID 178484047, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.1 g (13.35 mmol) trans-(4-methylaminomethyl-cyclohexyl)-methanol (example 1.1) were dissolved in 20 ml methanol. 3.32 g (13.35 mmol) N-(benzyloxycarbonyloxy)-succinimide were added and the solution was stirred at room temperature for 2 hours, then for 1 hour at 50° C. Afterwards, the solvent was evaporated under reduced pressure and the residue was partitioned between dichloromethane and water. The organic phase was washed with water (2 times), then with brine and finally dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on silica gel with a 4:1 v/v mixture of dichloromethane and diethyl ether as the eluent. 1.67 g (42.9%) trans-(4-hydroxymethyl-cyclohexylmethyl)-methyl-carbamic acid benzyl ester were obtained as colorless oil, M: 289 (M).

Workup

  1. waitfor 1 hour at 50° C
  2. customAfterwards, the solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between dichloromethane and water
  4. washThe organic phase was washed with water (2 times)
  5. dry with materialwith brine and finally dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silica gel with a 4:1 v/v mixture of dichloromethane and diethyl ether as the eluent

Sources & evidence

ORD record
ord-9aeb7f8b9d4648c193f8238a28b994b8
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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