Tetrahydrofuran → HCID 69023625, compound

HRID 1831923Notes

Reaction equation

HRID 1831923 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17]C(O)=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.C1C[O:34]CC1>>[C:1]([O:5][C:6](=[O:21])[NH:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][OH:34])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 14487Diisobutylaluminum hydrideHCID 69021387HCID 69021387, compound

Product 1

HCID 69023625HCID 69023625, compoundYield 68%

Procedure

To a −78° C. solution of 5-(carboxymethyl)-indole-1-carbamic acid tert-butyl ester (10.8 g, 39 mmol) in THF (180 mL) was added DIBAL (127 mL of a 1 M solution in THF, 127 mmol), and the reaction mixture was stirred for 2.5 h. The reaction was quenched with 1:11 N HCl/MeOH (100 mL), the reaction mixture was warmed to room temperature, diluted with CH2Cl2 (100 mL), and separated. The organic solution was washed with saturated Rochelle salt, dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:1 EtOAc/hexanes) provided 5-hydroxymethylindole-1-carbamic acid tert-butyl ester as a yellow oil (6.5 g, 68%): 1H NMR (300 MHz, CDCl3) δ 8.07 (d, J=9 Hz, 1H), 7.59 (d, J=6 Hz, 1H), 7.54 (s, 1H), 7.28 (d, J=9 Hz, 1H), 6.58 (d, J=6 Hz, 1H), 4.73 (s, 2H), 1.97 (s, 9H).

Workup

  1. customThe reaction was quenched with 1
  2. additiondiluted with CH2Cl2 (100 mL)
  3. customseparated
  4. washThe organic solution was washed with saturated Rochelle salt
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography (silica, 1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-85af95dfbd4c4909b46bf72581b9b6d7
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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