Cyclopentanemethanol → HCID 59656687, compound

HRID 2054907Notes

Reaction equation

HRID 2054907 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:18]=[C:17](F)[C:14]([C:15]#[N:16])=[C:13]([F:20])[CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:21]1([CH2:26][OH:27])[CH2:25][CH2:24][CH2:23][CH2:22]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.O>[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([F:20])[C:14]([C:15]#[N:16])=[C:17]([O:27][CH2:26][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:18]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 3

HCID 77195CyclopentanemethanolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 59656698HCID 59656698, compound

Product 1

HCID 59656687HCID 59656687, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the above benzonitrile intermediate (8.66 mmol) and cyclopentanemethanol (781 mg, 7.8 mmol) in THF (45 mL) at 0° C. was added N-sodium hexamethyldisilazane (1 M in THF, 7.8 mL, 7.8 mmol) and the reaction was stirred overnight. It was diluted with water, extracted with dichloromethane, washed with brine, dried with sodium sulfate, concentrated and dried in vacuo to give 4-(N-boc-2-aminoethyl)-2-cyclopentylmethoxy-6-fluorobenzonitrile (1.27 g, 3.5 mmol, 45%).

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b736579ffc9140efaf9d434665ed3f30
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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