Sodium hydride → HCID 57542646, compound

HRID 2080289Notes

Reaction equation

HRID 2080289 reaction equation
[H-].[Na+].[N:3]([CH2:6][C@@H:7]1[NH:11][C:10](=[O:12])[CH2:9][CH2:8]1)=[N+:4]=[N-:5].Br[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[N:3]([CH2:6][C@H:7]1[CH2:8][CH2:9][C:10](=[O:12])[N:11]1[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N+:4]=[N-:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 57542543HCID 57542543, compound

Product 1

HCID 57542646HCID 57542646, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To NaH (128 mg, 3.21 mmol) in DMF (5.0 mL) was added (R)-5-(azidomethyl)pyrrolidin-2-one (300 mg, 2.14 mmol) in DMF (5.0 mL) and stirred at rt for 30 min followed by addition of tert-butyl 3-bromopropylcarbamate. The mixture was heated to 60° C. for 2 h and quenched with sat. NH4Cl solution. The aqueous layer was extracted with EtOAc (50 mL×2) and the combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give (R)-tert-butyl 3-(2-(azidomethyl)-5-oxopyrrolidin-1-yl)propylcarbamate (358 mg of crude), which was used for next step without purification. LRMS (M+H+-Boc) m/z 198.1.

Workup

  1. temperatureThe mixture was heated to 60° C. for 2 h
  2. customquenched with sat. NH4Cl solution
  3. extractionThe aqueous layer was extracted with EtOAc (50 mL×2)
  4. washthe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-877bad087cc448cfa0fe2eb4517faf44
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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