tert-butyl N-(4-pyrrolidin-1-ylcyclohexyl)carbamate → Cyclohexanamine, 4-(1-pyrrolidinyl)-, trans-(9CI)

HRID 2234500Notes

Reaction equation

HRID 2234500 reaction equation
[N:1]1([CH:6]2[CH2:11][CH2:10][CH:9]([NH:12]C(=O)OC(C)(C)C)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[N:1]1([CH:6]2[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 21882609tert-butyl N-(4-pyrrolidin-1-ylcyclohexyl)carbamate2×

Product 1

HCID 21882596Cyclohexanamine, 4-(1-pyrrolidinyl)-, trans-(9CI)Yield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl N-(4-pyrrolidin-1-ylcyclohexyl)carbamate (Intermediate 238; 222 mg, 0.83 mmol) was taken up in DCM (1.5 mL) and TFA (1 mL). The reaction mixture was stirred at ambient temperature for 3 hours, poured directly onto an SCX-3 cartridge (2 g), pre-wet with DCM. The cartridge was washed through with DCM (10 mL), followed by methanol (30 mL) and then eluted with 2M ammonia in Methanol (25 mL). Evaporation to dryness of the ammoniacal solution yielded the title compound as an amber coloured oil (103 mg, 74%)

Workup

  1. washThe cartridge was washed through with DCM (10 mL)
  2. washeluted with 2M ammonia in Methanol (25 mL)
  3. customEvaporation to dryness of the ammoniacal solution

Sources & evidence

ORD record
ord-e58a8e05d0fa4b629029aa8b580a8f41
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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