Borane → HCID 69299659, compound

HRID 2196520Notes

Reaction equation

HRID 2196520 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[S:12][CH:13]=[C:14]([C:16]([NH2:18])=O)[N:15]=2)[N:9]=[C:8]([C:19]([F:22])([F:21])[F:20])[CH:7]=1.B.C1COCC1.B>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[S:12][CH:13]=[C:14]([CH2:16][NH2:18])[N:15]=2)[N:9]=[C:8]([C:19]([F:20])([F:21])[F:22])[CH:7]=1

Participants

5

Reactant 3

HCID 6331BoraneHCID 2723981Borane;tetrahydrofuranHCID 69300880HCID 69300880, compound

Product 1

HCID 69299659HCID 69299659, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 30 (317 mg, 0.966 mmol) in THF (966 μl) at 0° C. was added a solution of BH3.THF (1M in THF) (3.9 mL, 3.9 mmol). The resulting solution was allowed to stir for 4 h at room temperature. Then more borane.THF (1M in THF) (1 mL) was added. Stirring was continued for 16 h at room temperature. The mixture was quenched with methanol, and then solvent was evaporated to afford 31 (297 mg, 98%) as a yellow solid. LRMS (ESI): calc. 314.0; found 315.1 (MH)+.

Workup

  1. stirringStirring
  2. waitwas continued for 16 h at room temperature
  3. customThe mixture was quenched with methanol
  4. customsolvent was evaporated

Sources & evidence

ORD record
ord-6d702258a99946d59d3e36d05e282ab5
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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