Water → 3-(Phenylethynyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene

HRID 2040840Notes

Reaction equation

HRID 2040840 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH2:13][C:12]3([CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[O:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.O.[OH-].[Na+]>C(Cl)Cl>[C:1]1([C:7]#[C:8][C:9]2[CH2:13][C:12]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 57493807Tert-butyl 3-(phenylethynyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylate

Product 1

HCID 574938083-(Phenylethynyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of Compound 1b (200 mg, 0.59 mmol) in CH2Cl2 (12 mL) stirred at 0° C. was added trifluoroacetic acid (452 μl, 5.87 mmol) and the reaction mixture was stirred at 25° C. for 24 h, until the complete conversion of the reactant was observed by LC-MS. Water was added followed by 3N aq. NaOH to give a alkaline pH. Separation of the organic layer and extraction of the aqueous layer with CH2Cl2, washing with brine and drying over Na2SO4 the combined organic layers, afforded the title compound as beige solid, used in the next step without further purification.

Workup

  1. customto give a alkaline pH
  2. customSeparation of the organic layer and extraction of the aqueous layer with CH2Cl2
  3. washwashing with brine
  4. dry with materialdrying over Na2SO4 the combined organic layers

Sources & evidence

ORD record
ord-3be94343716d42ce89e8c417823b269c
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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