Carbon Disulfide → Ethyl 3-isothiocyanatopyrrolidine-1-carboxylate

HRID 1886388Notes

Reaction equation

HRID 1886388 reaction equation
O1CCCC1.[NH2:6][CH:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8]1.[C:17](=S)=[S:18]>>[N:6]([CH:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8]1)=[C:17]=[S:18]

Participants

4

Reactant 3

HCID 6348Carbon DisulfideHCID 8028TetrahydrofuranHCID 13656208Ethyl 3-aminopyrrolidine-1-carboxylate

Product 1

HCID 14575268Ethyl 3-isothiocyanatopyrrolidine-1-carboxylateYield 99.8%

Conditions

Temperature
-10 °C

Procedure

a-3) To a stirred and cooled (10° C.) mixture of 37 parts of N,N-methanetetraylbis[cyclohexanamine] and 594 parts of tetrahydrofuran were added 91.2 parts of carbon disulfide. After cooling to -10° C., 27.5 parts of ethyl 3-aminopyrrolidinecarboxylate were added during a period of 5 minutes (exothermic reaction). The reaction mixture was allowed to reach room temperature and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 32 parts (99.8%) of ethyl 3-isothiocyanato-1-pyrrolidinecarboxylate as a residue (interm. 6).

Workup

  1. temperaturecooled
  2. custom(exothermic reaction)
  3. customto reach room temperature
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated

Sources & evidence

ORD record
ord-89feac3aed8243adaabbc2ef4e2e26e7
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

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