Methanol → HCID 117871133, compound

HRID 1477150Notes

Reaction equation

HRID 1477150 reaction equation
[CH3:1][C:2]1([CH3:23])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]1[C:18]([O:20]CC)=[O:19].CO.[OH-].[Li+]>C1COCC1.O>[C:14]([O:13][C:11]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:23])([CH3:1])[CH:3]1[C:18]([OH:20])=[O:19])=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 117872132HCID 117872132, compound

Product 1

HCID 117871133HCID 117871133, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-tert-butyl 2-ethyl 3,3-dimethylindoline-1,2-dicarboxylate (0.25 g, 783 μmol, Eq: 1.00) in THF (3.2 mL)/MeOH (1.8 mL) was added lithium hydroxide (126 mg, 5.26 mmol, Eq: 6.72) dissolved in water (1 mL) and the resulting suspension was heated at 50° C. for 36 h. The reaction mixture was concentrated in vacuo and then the residue was taken up in water and washed with diethyl ether. The aqueous layer was then carefully acidified to pH˜3 with 1 M aqueous HCl and extracted with EtOAc. The combined organic layers were concentrated in vacuo to give 1-(tert-butoxycarbonyl)-3,3-dimethylindoline-2-carboxylic acid as a white foam (220 mg), m/z=292 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with diethyl ether
  3. extractionextracted with EtOAc
  4. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-e8e752540d8e4c3b960b2b620d7498c7
Source dataset
uspto-grants-2016_08
Patent number
US09403768B2

Reaction notes

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