Ammonium → HCID 86707550, compound

HRID 339074Notes

Reaction equation

HRID 339074 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]1[N:20]=[CH:19][C:18]([C:21](=O)[CH3:22])=[CH:17][CH:16]=1.[BH4-].[Na+].[NH4+]>C1COCC1.C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C.C(OCC)(=O)C.O.C(O)C>[F:14][C:15]1[N:20]=[CH:19][C:18]([CH:21]([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)[CH3:22])=[CH:17][CH:16]=1

Participants

10

Reactant 4

HCID 223AmmoniumHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 4311764Sodium borohydrideHCID 130903391-(6-Fluoropyridin-3-yl)ethan-1-one

Product 1

HCID 86707550HCID 86707550, compoundYield 44%

Reagents, catalysts & solvents 5

HCID 178460666HCID 178460666, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (0.94 g, 5.04 mmol), 1-(6-fluoropyridin-3-yl)ethanone (0.35 g, 2.52 mmol) in THF (10 mL) was added tetraisopropoxytitanium (1.48 mL, 5.04 mmol) and the reaction mixture was stirred at ambient temperature for 18 hours. Ethanol (2 mL) and NaBH4 (0.38 g, 10.1 mmol) were added and the mixture was stirred at ambient temperature for 2 hours. Water (10 mL), concentrated ammonium (2 mL) and ethyl acetate (20 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue obtained was purified by flash chromatography on silica gel (1:1 hexane/ethyl acetate) to give tert-butyl (3S)-1-(1-(6-fluoropyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (0.343 g, 44.0%) as solid.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 2 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by flash chromatography on silica gel (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2e451b7205104ef7aa048b8265d4bd09
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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