Hydrochloric Acid → HCID 53656559, compound

HRID 361304Notes

Reaction equation

HRID 361304 reaction equation
[N+:1]([C:4]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[C:10]=2[O:19][CH3:20])[CH2:7][CH2:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].Cl>C1COCC1.CO>[N+:1]([CH:4]1[CH2:5][CH2:6][CH2:7][CH:8]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[C:10]=1[O:19][CH3:20])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride3×HCID 54365300HCID 54365300, compound

Product 1

HCID 53656559HCID 53656559, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1.78 g (6.4 mmol) of 1-nitro-5-(2,3,4-trimethoxyphenyl)-cyclopentene in 40 mL of THF and 40 mL of methanol was cooled in an ice bath and a 0.35 g (9.2 mmol) portion of solid NaBH4 was added. The mixture was stirred for 1 h and 0.38 g (10.0 mmol) of solid NaBH4 was added. The mixture was stirred for 1 h and 0.37 g (9.8 mmol) of solid NaBH4 was added. After stirring for 1 h, 100 mL of 5% aqueous HCl was added and the bulk of the THF and methanol were removed in vacuo. The residue was extracted with two 100 mL portions of ether. The combined ether extracts were washed with 30 mL of brine, dried over MgSO4 and the solvent removed in vacuo to leave 1.37 g of an oil. The crude product was purified by flash chromatography on a column of 30 g of silica gel eluted successively with 100 mL portions of 0, 10, 20, 30, 40, 50 and 60% ether in hexanes to afford 0.68 g of a 1:1 mixture of cis- and trans-1-nitro-2-(2,3,4-trimethoxyphenyl)cyclopentane (Example 45).

Workup

  1. stirringThe mixture was stirred for 1 h
  2. stirringAfter stirring for 1 h
  3. customthe bulk of the THF and methanol were removed in vacuo
  4. extractionThe residue was extracted with two 100 mL portions of ether
  5. washThe combined ether extracts were washed with 30 mL of brine
  6. dry with materialdried over MgSO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b4320dfb74fb445eabc021f4f6e9937a
Source dataset
uspto-grants-1999_02
Patent number
US05866513

Reaction notes

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