Triethylamine → (S)-tert-Butyl 4-(3-(benzyloxycarbonylamino)pyrrolidin-1-yl)benzoate

HRID 1805281Notes

Reaction equation

HRID 1805281 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:19]=[CH:18][C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.CCN(CC)CC.[CH2:27]([O:34][C:35](Cl)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[CH2:27]([O:34][C:35]([NH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:19]=[CH:18][C:10]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 58930644HCID 58930644, compound

Product 1

HCID 59806000(S)-tert-Butyl 4-(3-(benzyloxycarbonylamino)pyrrolidin-1-yl)benzoateYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of compound 17 (4.37 g, 16.72 mmol) in THF (30 mL) was cooled to 0° C. and treated successively with Et3N (4.6 mL, 3.38 g, 33 mmol) and benzylchloroformate (2.8 mL, 3.42 g, 20 mmol). The reaction mixture was allowed to stir for 2 hrs at 0° C., quenched by adding an aqueous saturated NH4Cl solution (30 mL) and extracted with EtOAc. The extract was dried over Na2SO4, filtered and concentrated. Crude product was purified by flash chromatography using 30% EtOAc in hexanes as an eluent to provide title compound 115 (3 g, 45% yield). LRMS (ESI): (calc) 396.20 (found) 397.2 (MH)+.

Workup

  1. customquenched
  2. additionby adding an aqueous saturated NH4Cl solution (30 mL)
  3. extractionextracted with EtOAc
  4. dry with materialThe extract was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customCrude product was purified by flash chromatography

Sources & evidence

ORD record
ord-bf005644ad8d4ea38755b990a7d11d34
Source dataset
uspto-grants-2013_01
Patent number
US08354445B2

Reaction notes

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