Triethylamine → 3-[(6-Chloro-benzooxazol-2-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 222411

Reaction equation

HRID 222411 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH2:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[O:17][C:18]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:19]=2[N:20]=1.CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:16]2[O:17][C:18]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:19]=3[N:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 771752,6-DichlorobenzoxazoleHCID 2756485tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 591780113-[(6-Chloro-benzooxazol-2-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 220 mg (1.1 mmol) 3-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (commercially available), 188 mg (1 mmol) 2,6-dichloro-benzooxazole (commercially available) and 303 mg (3 mmol) NEt3 in 4 mL DCM was stirred at room temperature over night. After evaporation to dryness the residue was purified with flash column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane. The product containing fractions were evaporated to yield 351 mg (99%) of the title compound. MS (m/e): 352.4 (MH+).

Workup

  1. customAfter evaporation to dryness the residue
  2. customwas purified with flash column chromatography on silica eluting with a gradient
  3. customformed from ethyl acetate and heptane
  4. additionThe product containing fractions
  5. customwere evaporated

Sources & evidence

ORD record
ord-8372c10d7a794a2eaee5d4b9279258a4
Source dataset
uspto-grants-2012_06
Patent number
US08207220B2

Linked notes

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