Lithium Hydroxide → 2-(2-allyl-1-(tert-butoxycarbonyl)-1H-indol-3-yl)acetic acid

HRID 1471645Notes

Reaction equation

HRID 1471645 reaction equation
[CH2:1]([C:4]1[N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:6]2[C:11]([C:12]=1[CH2:13][C:14]([O:16]C)=[O:15])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[CH2:3].[Li+].[OH-]>C1COCC1.CO.O>[CH2:1]([C:4]1[N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:6]2[C:11]([C:12]=1[CH2:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 90281273tert-butyl 2-allyl-3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate

Product 1

HCID 902812522-(2-allyl-1-(tert-butoxycarbonyl)-1H-indol-3-yl)acetic acidYield 104.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-allyl-3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate (0.94 g, 2.74 mmol) in THF (15 mL) and MeOH (5 mL) was added a solution of LiOH (170 mg, 6.8 mmol) in H2O (5 mL). The solution was stirred for 2 h. The reaction was partitioned between EtOAc and 20% aqueous KH2PO4. The organics were separated, dried over sodium sulfate, and the solvents removed in vacuo to provide 2-(2-allyl-1-(tert-butoxycarbonyl)-1H-indol-3-yl)acetic acid (900 mg). MS (m/z) 316 [M+H]+.

Workup

  1. customThe reaction was partitioned between EtOAc and 20% aqueous KH2PO4
  2. customThe organics were separated
  3. dry with materialdried over sodium sulfate
  4. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-7418bb0dac4a44cf8c658462d3011263
Source dataset
uspto-grants-2015_04
Patent number
US09012441B2

Reaction notes

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