Ethanol → HCID 21250279, compound

HRID 1531741Notes

Reaction equation

HRID 1531741 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16].C(O)C.[BH4-].[Na+]>C(OCC)(=O)C>[CH:1]1([NH:12][C:11]2[CH:13]=[CH:14][C:8]([F:7])=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8452CyclopentanoneHCID 677684-Fluoro-3-nitroanilineHCID 4311764Sodium borohydride

Product 1

HCID 21250279HCID 21250279, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6.7 g (0.08 mol) of cyclopentanone, 12.5 g (0.08 mol) of 4-fluoro-3-nitro-aniline and 30 ml (0.1 mol) of titanium-IV-isopropoxide are stirred for 30 minutes at 40° C. and one hour at ambient temperature. After the addition of 150 ml of ethanol the reaction mixture is stirred for 30 minutes and subsequently combined batchwise with 2.4 g (0.066 mol) of sodium borohydride. After 4 hours the reaction mixture is poured onto ice water and combined with ethyl acetate. After filtration the organic phase is separated off, dried and evaporated down. The residue is chromatographed on silica gel and eluted with petroleum ether/ethyl acetate (9:1). The desired fractions are combined and evaporated down.

Workup

  1. additionAfter 4 hours the reaction mixture is poured onto ice water
  2. filtrationAfter filtration the organic phase
  3. customis separated off
  4. customdried
  5. customevaporated down
  6. customThe residue is chromatographed on silica gel
  7. washeluted with petroleum ether/ethyl acetate (9:1)
  8. customevaporated down

Sources & evidence

ORD record
ord-b839803533734933a2ece87db9cbaa65
Source dataset
uspto-grants-2001_03
Patent number
US06200976B1

Reaction notes

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