(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → HCID 57970134, compound

HRID 1666669Notes

Reaction equation

HRID 1666669 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.[F:14][C:15]([F:28])([F:27])[O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](O)=[O:25])=[CH:19][CH:18]=1.CCN=C=NCCCN(C)C.Cl>C1COCC1>[F:14][C:15]([F:27])([F:28])[O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][C:24]([N:1]2[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]2)=[O:25])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27773192-[4-(Trifluoromethoxy)phenyl]acetic acid

Product 1

HCID 57970134HCID 57970134, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of t-butyl (S)pyrrolidin-3-ylcarbamate (93 g), 4-trifluoromethoxyphenylacetic acid (112 g), and THF (550 mL) were added EDC.HCl (114 g) and HOBt-1H2O (114 g), and the mixture was stirred at room temperature for 3 days. The reaction solution was concentrated under reduced pressure, then diluted with chloroform, and washed with saturated aqueous sodium hydrogencarbonate, water, and brine. The organic layer was dried with anhydrous magnesium sulfate, then the desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting solids were washed with chloroform to obtain t-butyl ((S)-1-(2-(4-trifluoromethoxyphenyl)ethanoyl)pyrrolidin-3-yl)carbamate (144 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with chloroform
  3. washwashed with saturated aqueous sodium hydrogencarbonate, water, and brine
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. customthe desiccant was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washThe resulting solids were washed with chloroform

Sources & evidence

ORD record
ord-72e4a3626f514246955d5f18bc81dbf5
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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