5-Nitro-2,3-dihydro-1H-indene-2-carboxylic acid → HCID 25139893, compound

HRID 1669101Notes

Reaction equation

HRID 1669101 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([C:13](O)=[O:14])[CH2:7]2)([O-:3])=[O:2]>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][OH:14])[CH2:7]2)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 185458885-Nitro-2,3-dihydro-1H-indene-2-carboxylic acid

Product 1

HCID 25139893HCID 25139893, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

BH3-DMS (10 M, 1.30 mL, 13.0 mmol) was added to a stirred solution of acid 119 (2.07 g, 10.0 mmol) in dry THF (30 mL) at 20° C. under N2 and the mixture was stirred at 20° C. for 30 min. The reaction was quenched with MeOH and the solvent evaporated to give a brown oil which was purified by chromatography, eluting with a gradient (0-20%) of EtOAc/pet. ether, to give alcohol 120 (1.13 g, 59%) as an oil: 1H NMR δ 8.01-8.07 (m, 2H, H-4, H-6), 7.32 (d, J=8.0 Hz, 1H, H-7), 3.68 (d, J=5.8 Hz, 2H, CH2O), 3.09-3.20 (m, 2H, CH2), 2.76-2.91 (m, 3H, CH2, CH); HRMS calcd for C10H11NO3 (M+) m/z 193.0739, found 193.0733.

Workup

  1. customThe reaction was quenched with MeOH
  2. customthe solvent evaporated
  3. customto give a brown oil which
  4. customwas purified by chromatography
  5. washeluting with a gradient (0-20%) of EtOAc/pet. ether

Sources & evidence

ORD record
ord-e21a4b523c4f445d97050fb226f2c453
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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