Cyclopentanone → HCID 118115144, compound

HRID 1050572Notes

Reaction equation

HRID 1050572 reaction equation
[C:1]([C:3]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)#[N:2].[C:23]1(=O)[CH2:27][CH2:26][CH2:25][CH2:24]1.[BH3-]C#N.[Na+]>CO.CC(O)=O>[C:1]([C:3]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[CH:11][CH:10]=2)[CH2:4][CH2:5][N:6]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:7][CH2:8]1)#[N:2]

Participants

6

Reactant 3

HCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 118114536HCID 118114536, compound

Product 1

HCID 118115144HCID 118115144, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Compound 348 (230 mg, 0.77 mmol) was dissolved in 20 mL MeOH and 1 mL HOAc. To the solution was added cyclopentanone (280 μL, 3.08 mmol) and the mixture was stirred at RT for 2.5 hours. Then NaBH3CN (290 mg, 4.62 mmol) was added, and the mixture was stirred at RT for overnight. It was concentrated in vacuo, diluted with EtOAc 150 mL, washed with 1N NaOH and water, dried, concentrated in vacuo to dryness to give crude tert-butyl 4-(4-cyano-1-cyclopentylpiperidin-4-yl)phenylcarbamate (349, 280 mg, 98%). It was treated with 4N HCl in dioxane at RT for 4 hours and concentrated in vacuo to dryness to give 4-(4-aminophenyl)-1-cyclopentylpiperidine-4-carbonitrile hydrochloride (350, 250 mg, quantitative yield).

Workup

  1. stirringthe mixture was stirred at RT for overnight
  2. concentrationIt was concentrated in vacuo
  3. additiondiluted with EtOAc 150 mL
  4. washwashed with 1N NaOH and water
  5. customdried
  6. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-fd858f162d3645ea8dd2cf93a83b4fdc
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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