Lithium tri-s-butylborohydride → HCID 86689842, compound

HRID 2409028Notes

Reaction equation

HRID 2409028 reaction equation
[C:1]([S@:5]([N:7]=[C:8]([C:10]1[N:11]=[CH:12][C:13]2[N:18](C(OCC)=O)[CH:17]=[CH:16][C:14]=2[N:15]=1)[CH3:9])=[O:6])([CH3:4])([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[N:15]1[C:14]2[CH:16]=[CH:17][NH:18][C:13]=2[CH:12]=[N:11][C:10]=1[CH:8]([NH:7][S@@:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[O:6])[CH3:9]

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 86689843HCID 86689843, compound

Product 1

HCID 86689842HCID 86689842, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To (R)-ethyl 2-(1-(tert-butylsulfinylimino)ethyl)-5H-pyrrolo[3,2-d]pyrimidine-5-carboxylate (259.0 mg, 0.77 mmol) in anhydrous THF (5 mL) at 0° C. was added dropwise L-selectride (1.0 mol/L) in THF (1.2 mL). The resultant orange reaction mixture was warmed to RT and stirred under N2 for 16 h. The solvent was removed in vacuo and the crude was partitioned between EtOAc and water. The organic layer was washed with sat'd. aq. NaHCO3, water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude was purified by SiO2 chromatography eluted with a mixture of EtOAc containing 1% TEA and MeOH to afford 180.0 mg (87.8%) of (R)—N-(1-(5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethyl)-2-methylpropane-2-sulfinamide as racemic mixture. MS (ESI) m/z: 267 [M+1]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude was partitioned between EtOAc and water
  3. washThe organic layer was washed with sat'd
  4. dry with materialaq. NaHCO3, water and brine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by SiO2 chromatography
  8. washeluted with a mixture of EtOAc containing 1% TEA and MeOH

Sources & evidence

ORD record
ord-5584f7e4c83f4be7a694101014d186df
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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