Tetrahydrofuran → 5-(2-Hydroxy-ethyl)-indole-1-carboxylic acid tert-butyl ester

HRID 2361898Notes

Reaction equation

HRID 2361898 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=[CH2:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B1C2CCCC1CCC2.C1C[O:31]CC1>O.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH2:18][OH:31])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 789669-Borabicyclo(3.3.1)nonaneHCID 66890900tert-Butyl 5-ethenyl-1H-indole-1-carboxylate

Product 1

HCID 668908615-(2-Hydroxy-ethyl)-indole-1-carboxylic acid tert-butyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-vinyl-indole-1-carboxylic acid tert-butyl ester (4.5 g, 18.5 mmol, 1.0 eq.) in THF (46 mL) at 0° C. was added 9-BBN (0.5 M in THF, 87 mL, 2.4 eq.) over 10 min. The resulting reaction mixture was stirred for 2.5 h and diluted with THF (150 mL) and water (150 mL) while keeping the temperature at 0° C. Then NaBO3.4H2O (44 g) was introduced and resulting reaction mixture was stirred and warmed to room temperature and stirred. The reaction mixture was diluted with methylene chloride (100 mL) and the separated aqueous layer was extracted 3×100 mL methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography (methylene chloride to 5% acetone/methylene chloride) to give 5-(2-hydroxy-ethyl)-indole-1-carboxylic acid tert-butyl ester (3.82 g, 76%) or similarly 6-(2-hydroxy-ethyl)-indole-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe resulting reaction mixture
  2. customat 0° C
  3. customresulting
  4. customreaction mixture
  5. stirringwas stirred
  6. stirringstirred
  7. extractionthe separated aqueous layer was extracted 3×100 mL methylene chloride
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography (methylene chloride to 5% acetone/methylene chloride)

Sources & evidence

ORD record
ord-8d432eb7f38449c7a7675de36f1d0619
Source dataset
uspto-grants-2014_04
Patent number
US08691814B2

Reaction notes

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