Ethyl Acetate → HCID 18535987, compound

HRID 412167Notes

Reaction equation

HRID 412167 reaction equation
[C:1]([C:3]1[CH:41]=[CH:40][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[CH:26]=[C:25]([O:27][CH2:28][CH:29]=[CH2:30])[CH:24]=[CH:23][C:22]=4[O:31]CC4C=CC=CC=4)[C:16](=[O:39])[CH2:15]3)=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:42])#[N:2].[BH4-].[Na+].CCOC(C)=O>C1COCC1.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:41]=[CH:40][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[CH:26]=[C:25]([O:27][CH2:28][CH:29]=[CH2:30])[CH:24]=[CH:23][C:22]=4[OH:31])[C:16](=[O:39])[CH2:15]3)=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:42])#[N:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 18535999HCID 18535999, compound

Product 1

HCID 18535987HCID 18535987, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step G (800 mg, 1.38 mmol) in 20 mL of THF at room temperature was added Pd(PPh3)4 (203 mg, 0.176 mmol), followed by sodium borohydride (86.2 mg, 2.28 mmol). The reaction was stirred for several hours, then poured into EtOAc and washed with water, saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was taken up in methanol, filtered, and the solids were dried in vacuo to afford the titled product as an off-white solid.

Workup

  1. washwashed with water, saturated NaHCO3 solution and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. filtrationfiltered
  6. customthe solids were dried in vacuo

Sources & evidence

ORD record
ord-b36c58c465a64158b1731769d9b43153
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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