3-Azidoacetyl-1-(tert-butoxycarbonyl)-indole → 3-Aminoacetyl-1-(tert-butoxycarbonyl)-indole

HRID 583782Notes

Reaction equation

HRID 583782 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:8]=1)=[O:6])=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.[Pd]>[NH2:1][CH2:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:8]=1)=[O:6]

Participants

5

Reactant 2

HCID 108702993-Azidoacetyl-1-(tert-butoxycarbonyl)-indoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 223425203-Aminoacetyl-1-(tert-butoxycarbonyl)-indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-azidoacetyl-1-(tert-butoxycarbonyl)-indole (0.01 mol), which may be prepared as described in Step (d) above, in THF is added a reducing agent such as, for example, a catalytic amount (0.0001 to 0.001 mol) of a hydrogenolysis catalyst such as, for example, 10% palladium on carbon, and the mixture is shaken under a hydrogen atmosphere at from atmospheric pressure to about 75 psi. (Alternatively, other reducing agents such as lithium aluminum hydride may be used. Reaction work-up conditions may be modified according to the reduction reaction employed.) Reaction progress may be followed by TLC or HPLC. When a sufficient amount of desired product is formed, the mixture is filtered, optionally through a filter aid such as, for example, CELITE (Celite Products Company, Los Angeles, Calif.), and the filter cake is washed with additional solvent (THF). The filtrate and washings rotary evaporated to give 3-aminoacetyl-1-(tert-butoxycarbonyl)-indole, which may be purified, if needed or desired, by chromatography on silica gel or crystallization. Alternatively, the 3-aminoacetyl-1-(tert-butoxycarbonyl)-indole can be dissolved in ethyl ether, which optionally contains minor amounts (i.e., <50% v/v) of THF, and 1 mol equivalent of a solution of either hydrogen chloride in ethyl ether or concentrated hydrochloric acid is added. The solid 3-aminoacetyl-1-(tert-butoxycarbonyl)-indole hydrochloride which precipitates, or if little or no solid precipitates, the 3-aminoacetyl-1-(tert-butoxycarbonyl)-indole hydrochloride obtained upon rotary evaporation of the mixture, may be purified, if needed or desired, by crystallization.

Workup

  1. additionis added a reducing agent such as, for example
  2. customReaction work-up conditions
  3. custommay be modified according to the reduction reaction
  4. custom) Reaction progress

Sources & evidence

ORD record
ord-960f59c0afcd4821ba9395f82b05380b
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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