Potassium;tri(butan-2-yl)boranuide → HCID 69890897, compound

HRID 2088110Notes

Reaction equation

HRID 2088110 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[C:15]([C@@H:17]1[C@:23]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]([CH2:25][CH:26]=[CH2:27])[C@H:19]([CH:20]=[CH:21][C:22]2=[O:34])[CH2:18]1)#[N:16]>C1COCC1>[C:15]([C@@H:17]1[C@:23]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]([CH2:25][CH:26]=[CH2:27])[C@@H:19]([CH2:20][CH2:21][C@H:22]2[OH:34])[CH2:18]1)#[N:16]

Participants

4

Reactant 2

HCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 69889607HCID 69889607, compound

Product 1

HCID 69890897HCID 69890897, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of K-Selectride® in THF (1M, 6.5 ml, 6.5 mmol) was added dropwise to a stirred solution of (1R*,5S*,7S*)-7-cyano-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]oct-3-en-2-one (Description 23c; 295 mg, 1.11 mmol) in THF (7 ml) at −78° C. The reaction mixture was slowly warm up to +15° C. over 6 hours and carefully quenched with a mixture of 2M NaOH (8 ml) and H2O2 (35%, 2 ml). The mixture was stirred for 20 minutes. The mixture was treated with saturated aqueous Na2SO3 and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate) to give the title compound (50 mg, 17%).

Workup

  1. temperatureThe reaction mixture was slowly warm up to +15° C. over 6 hours
  2. customcarefully quenched with a mixture of 2M NaOH (8 ml) and H2O2 (35%, 2 ml)
  3. additionThe mixture was treated with saturated aqueous Na2SO3
  4. extractionextracted into dichloromethane
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate)

Sources & evidence

ORD record
ord-28b3c710756042fb9c0aeb8facb00648
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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