Cyclopentanone → HCID 11619765, compound

HRID 734797Notes

Reaction equation

HRID 734797 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:29]=[CH:28][C:19]([O:20][CH2:21][CH2:22][NH:23][CH2:24][CH:25]4[CH2:27][CH2:26]4)=[CH:18][CH:17]=3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[C:30]1(=O)[CH2:34][CH2:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(O)=O.C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([O:20][CH2:21][CH2:22][N:23]([CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[CH2:24][CH:25]4[CH2:27][CH2:26]4)=[CH:28][CH:29]=3)=[N:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8452Cyclopentanone2×HCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 69065035HCID 69065035, compound

Product 1

HCID 11619765HCID 11619765, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 80.6 mg (0.20 mmol) of (2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenoxy}ethyl)cyclopropylmethylamine, 35 μL (0.40 mmol) of cyclopentanone, and one drop of AcOH in 10 mL of THF was stirred for 15 minutes. 169.5 mg (0.80 mmol) of sodium triacetoxyborohydride was added and the mixture was stirred for 24 hours at RT. A further 17.5 μL of cyclopentanone and 85 mg of sodium triacetoxyborohydride were added and the mixture was again stirred for 24 hours at RT. The reaction mixture was diluted with water, made basic with saturated aqueous potassium carbonate solution, and the aqueous phase was extracted with EtOAc. The combined organic phases were dried over sodium sulfate and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, EtOAc/MeOH/conc. aqueous ammonia 98:2:0.2) and stirred with DIPE. Yield: 22 mg (23% of theoretical); C30H31ClN2O (M=471.033); calc.: molpeak (M+H)+: 471/473 (Cl); found: molpeak (M+H)+: 471/473 (Cl); HPLC-MS: 5.83 minutes (method B).

Workup

  1. stirringthe mixture was stirred for 24 hours at RT
  2. stirringthe mixture was again stirred for 24 hours at RT
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated down in vacuo
  6. customThe crude product was purified by column chromatography (silica gel, EtOAc/MeOH/conc. aqueous ammonia 98:2:0.2)
  7. stirringstirred with DIPE
  8. custom5.83 minutes (method B)

Sources & evidence

ORD record
ord-b9a5ad4193e344839ac097b0b9c67ffa
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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