Lithium tri-s-butylborohydride → HCID 86689831, compound

HRID 2409019Notes

Reaction equation

HRID 2409019 reaction equation
[C:1]([S@:5]([N:7]=[C:8]([C:10]1[N:15]=[C:14]2[CH:16]=[CH:17][N:18](C(OC(C)(C)C)=O)[C:13]2=[CH:12][CH:11]=1)[CH3:9])=[O:6])([CH3:4])([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[NH:18]1[C:13]2[C:14](=[N:15][C:10]([C@@H:8]([NH:7][S@@:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[O:6])[CH3:9])=[CH:11][CH:12]=2)[CH:16]=[CH:17]1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 86689830HCID 86689830, compound

Product 1

HCID 86689831HCID 86689831, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-tert-butyl 5-(1-(tert-butylsulfinylimino)ethyl)-1H-pyrrolo[3,2-b]-pyridine-1-carboxylate (1.18 g, 3.25 mmol) in anhydrous THF (21.1 mL) at 0° C. was added dropwise L-selectride (1.0 mol/L) in THF (4.9 mL). The resultant orange reaction mixture was warmed to RT and stirred under N2 for 3 h. The solvent was removed in vacuo, and the crude product was purified by SiO2 chromatography eluting with MeOH/EtOAc+1% TEA to afford 700 mg (81.3%) of (R)—N—((S)-1-(1H-pyrrolo[3,2-b]-pyridin-5-yl)ethyl)-2-methylpropane-2-sulfinamide as a foam (95% ee). The enantiomers were separated via chiral SFC chromatography to give 597.0 mg (100% ee) of (R)—N—((S)-1-(1H-pyrrolo[3,2-b]-pyridin-5-yl)ethyl)-2-methylpropane-2-sulfinamide: 1H NMR (400 MHz, MeOD) δ 7.79 (d, J=8.5 Hz, 1H), 7.55 (d, J=3.3 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 6.58 (d, J=3.1 Hz, 1H), 4.73-4.66 (m, 1H), 1.63 (d, J=6.9 Hz, 3H), 1.19 (s, 9H); MS (ESI) m/z: 266.3 [M+1]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified by SiO2 chromatography
  3. washeluting with MeOH/EtOAc+1% TEA

Sources & evidence

ORD record
ord-70fef64ce6144e928da90e5d3c65cbba
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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