Lithium borohydride → HCID 58763424, compound

HRID 858288Notes

Reaction equation

HRID 858288 reaction equation
[Li+].[BH4-].[C:3]([C:6]1[CH:7]=[C:8]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][C:22](OCC)=[O:23])=[C:13]2[C:27]([OH:29])=[O:28])[CH:9]=[CH:10][CH:11]=1)([OH:5])=[O:4]>COCCOC>[C:3]([C:6]1[CH:7]=[C:8]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][CH2:22][OH:23])=[C:13]2[C:27]([OH:29])=[O:28])[CH:9]=[CH:10][CH:11]=1)([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58763425HCID 58763425, compound

Product 1

HCID 58763424HCID 58763424, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a suspension of LiBH4 (0.157 g, 7.2 mmol) in anhydrous DME (50 mL) was added a solution of 1-(3-carboxy-phenyl)-3-ethoxycarbonylmethyl-1H-indole-2-carboxylic acid in DME containing 3% methanol (10 mL). The reaction mixture was heated at reflux for 1 h and then allowed to cool to room temperature. The reaction was quenched with 1 N HCl at 0° C. and extracted with EtOAc. The extract was dried over Na2SO4 and concentrated to afford 0.78 g of 1-(3-carboxy-phenyl)-3-(2-hydroxyethyl)-1H-indole-2-carboxylic acid as a yellow oil (100% crude yield): 1H NMR (CDCl3, 300 MHz) δ 3.28 (t, J=6.87 Hz, 2H), 3.69 (t, J=6.87 Hz, 2H), 7.03 (d, J=8.20 Hz, 1H); 7.18(t, J=7.25 Hz, 1H), 7.28 (t, J=7.25 Hz, 1H), 7.60–7.68 (m, 2H), 7.76–7.81 (m, 2H), 8.02 (d, J=7.06 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. customThe reaction was quenched with 1 N HCl at 0° C.
  4. extractionextracted with EtOAc
  5. dry with materialThe extract was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a4395f912e34485fb9e0f9d1bae64342
Source dataset
uspto-grants-2006_12
Patent number
US07148250B2

Reaction notes

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