N-(tert-Butoxycarbonyl)-1,5-diaminopentane → tert-Butyl N-(5-isothiocyanatopentyl)carbamate

HRID 2119598Notes

Reaction equation

HRID 2119598 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])([CH3:4])([CH3:3])[CH3:2].[C:15](=S)=[S:16].N#CN>C1COCC1.CCN(CC)CC>[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]=[C:15]=[S:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 6348Carbon DisulfideHCID 9864Cyanamide

Product 1

HCID 3340418tert-Butyl N-(5-isothiocyanatopentyl)carbamateYield 93%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2 g (9.9 mmol) (5-Amino-pentyl)-carbamic acid tert-butyl ester in 40 ml THF at 0° C. was added 896 μl (14.83 mmol) CS2 and allowed to stir at room temperature for 14 h. 623 mg (14.83 mmol) cyanamide and 4 drops NEt3 was added and the mixture was heated to 4° C. for 3 h. The mixture was extracted with diethyl ether and the combined organic layers were dried with MgSO4. After filtration and removal of the volatiles the residue was purified by flash column chromatography on silica eluting with ethyl acetate/cyclohexane 1:1. The evaporation of the product fractions yielded 2.24 g (93%) of the title compound.

Workup

  1. temperaturethe mixture was heated to 4° C. for 3 h
  2. extractionThe mixture was extracted with diethyl ether
  3. dry with materialthe combined organic layers were dried with MgSO4
  4. filtrationAfter filtration and removal of the volatiles the residue
  5. customwas purified by flash column chromatography on silica eluting with ethyl acetate/cyclohexane 1:1
  6. customThe evaporation of the product fractions

Sources & evidence

ORD record
ord-a634be2f1763409bba251bce0f0dbe8f
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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