Iodine → HCID 66673659, compound

HRID 423409Notes

Reaction equation

HRID 423409 reaction equation
II.[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=O)[CH2:17][O:18]C)[CH2:11]2)=[N:8][CH:9]=1.[BH4-].[Na+]>O1CCCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][CH2:16][CH2:17][OH:18])[CH2:11]2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 807IodineHCID 4311764Sodium borohydrideHCID 66673692HCID 66673692, compound

Product 1

HCID 66673659HCID 66673659, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add dropwise via an addition funnel a solution of iodine (727 mg, 2.86 mmol) in tetrahydrofuran (5 mL) over 15 min to a mixture of N—[(R)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl]-2-methoxy-acetamide (500 mg, 1.59 mmol) and sodium borohydride (217 mg, 6.05 mmol) in tetrahydrofuran (5 mL). Heat the colorless mixture at reflux overnight, then cool to room temperature and slowly quench with MeOH until no foaming is observed. Concentrate the material in vacuo. Add 1N NaOH (20 mL) to the residue and extract the mixture with dichloromethane (3×20 mL). Dry the combined organics over Na2SO4, filter, and concentrate to dryness. Purify using chromatography (0 to 10% MeOH/CH2Cl2) to afford 120 mg (26%) of the title compound. LC-MS/ES m/z (79Br) 286.2 [M+H]+.

Workup

  1. temperatureHeat the colorless mixture
  2. temperatureat reflux overnight
  3. customslowly quench with MeOH until no foaming
  4. concentrationConcentrate the material in vacuo
  5. additionAdd 1N NaOH (20 mL) to the residue
  6. extractionextract the mixture with dichloromethane (3×20 mL)
  7. dry with materialDry the combined organics over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate to dryness
  10. customPurify

Sources & evidence

ORD record
ord-09b8cc84c3df4a578f94f5613e79fc09
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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