Tetrabutylammonium Fluoride → HCID 57605188, compound

HRID 2116729Notes

Reaction equation

HRID 2116729 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH2:11][C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([O:21][Si](C(C)(C)C)(C)C)[CH:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH2:11][C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([OH:21])[CH:15]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68948944HCID 68948944, compound

Product 1

HCID 57605188HCID 57605188, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

[6-(tert-Butyl-dimethyl-silanyloxy)-1H-indol-2-ylmethyl]-carbamic acid benzyl ester (0.80 g, 1.95 mmol) is dissolved in THF (2 ml). Cooled to −78° C. 1 M TBAF solution in THF (3.90 ml) is added. The reaction mixture is concentrated and the residue is purified by column chromatography (30% ethyl acetate in hexanes) to obtain (6-Hydroxy-1H-indol-2-ylmethyl)-carbamic acid benzyl ester.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is purified by column chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1d8bb89a9df442adb73e23d1ccddc0d6
Source dataset
uspto-grants-2008_10
Patent number
US07439249B2

Reaction notes

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