Sodium borohydride → HCID 178432785, compound

HRID 412156Notes

Reaction equation

HRID 412156 reaction equation
[C:1]([C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[N:26]=[C:25]([O:27]CC=C)[CH:24]=[CH:23][CH:22]=4)[C:16](=[O:31])[CH2:15]3)=[CH:11][N:10]=[C:9]2[CH3:32])=[CH:5][C:4]=1[F:35])#[N:2].[BH4-].[Na+]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[N:26]=[C:25]([OH:27])[CH:24]=[CH:23][CH:22]=4)[C:16](=[O:31])[CH2:15]3)=[CH:11][N:10]=[C:9]2[CH3:32])=[CH:5][C:4]=1[F:35])#[N:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18536090HCID 18536090, compound

Product 1

HCID 178432785HCID 178432785, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the allyl ether from Step E (89.6 mg, 0.189 mmol) in 2 mL of tetrahydrofuran was added tetrakis(triphenylphosphine)palladium (4.3 mg, 0.0037 mmol). After 5 minutes, sodium borohydride was added (10.7 mg, 0.283 mmol), and the reaction was stirred at room temperature for 30 minutes. The reaction was quenched with saturated NH4Cl solution, then partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the desired product as a yellow foam.

Workup

  1. customThe reaction was quenched with saturated NH4Cl solution
  2. custompartitioned between EtOAc and saturated NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e506c74afbb7497389a87e1215975695
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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