Cyclopentylamine → HCID 178471909, compound

HRID 561097Notes

Reaction equation

HRID 561097 reaction equation
[CH3:1][O:2][C:3]1[C:4]([F:19])=[C:5]([CH:14]=[C:15]([F:18])[C:16]=1[F:17])[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7].[CH3:20]C(OC(C)=O)=O.C(OCC)(OCC)OCC.[CH:37]1([NH2:42])[CH2:41][CH2:40][CH2:39][CH2:38]1>>[CH3:1][O:2][C:3]1[C:4]([F:19])=[C:5]([CH:14]=[C:15]([F:18])[C:16]=1[F:17])[C:6]([C:8](=[CH:20][NH:42][CH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7]

Participants

5

Reactant 4

HCID 2906CyclopentylamineHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 10588473Ethyl 3-oxo-3-(2,4,5-trifluoro-3-methoxyphenyl)propanoate

Product 1

HCID 178471909HCID 178471909, compoundYield 95.2%

Procedure

A solution of ethyl (3-methoxy-2,4,5-trifluorobenzoyl)acetate (12, 7.6 g, 27.5 mmol), Ac2O (6.5 mL, 69 mmol) and triethyl orthoformate (6.9 mL, 41 mmol) was heated at 150° C. for 1.5 h. The mixture was concentrated in vacuo and dried under high vacuum for 3 hours. The crude product 13 was dissolved in ethanol (50 mL) and cyclopentyl amine (2.8 mL, 27 mmol) was added very slowly at 0° C. After 1.5 h, the solvent was removed by evaporation to yield 14 as a dark yellow solid (9.55 g crude, quantitative).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customdried under high vacuum for 3 hours
  3. dissolutionThe crude product 13 was dissolved in ethanol (50 mL)
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-2dae2434572d41a0b517e7b28bd5e4e5
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

Loading…