Lithium Hydroxide → HCID 58551346, compound

HRID 2204254Notes

Reaction equation

HRID 2204254 reaction equation
[CH2:1]([C:3]1[CH:32]=[CH:31][C:6]([C:7]([N:9]2[CH2:30][CH2:29][C:12]3([C:17]4=[CH:18][CH:19]=[CH:20][N:16]4[C:15]4[CH:21]=[CH:22][C:23]([C:25]([O:27]C)=[O:26])=[CH:24][C:14]=4[O:13]3)[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[O:33][CH3:34])[CH3:2].[Li+].[OH-]>O1CCOCC1.C(OCC)(=O)C>[CH2:1]([C:3]1[CH:32]=[CH:31][C:6]([C:7]([N:9]2[CH2:10][CH2:11][C:12]3([O:13][C:14]4[CH:24]=[C:23]([C:25]([OH:27])=[O:26])[CH:22]=[CH:21][C:15]=4[N:16]4[CH:20]=[CH:19][CH:18]=[C:17]34)[CH2:29][CH2:30]2)=[O:8])=[CH:5][C:4]=1[O:33][CH3:34])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58550869HCID 58550869, compound

Product 1

HCID 58551346HCID 58551346, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 1-(4-ethyl-3-methoxy-benzoyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-7′-carboxylate (1.1 g, 2.5 mmol) in LiOH (2.5 mL of 4.0 M, 9.9 mmol) and dioxane (5 mL) was stirred at 50° C. for 1 hour. The reaction was diluted with ethyl acetate and washed with water. The aqueous was acidified with 1N HCl and the product was extracted into ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated to yield a crude product that was used in the next step without further purification (0.60 g, 53%). ESI-MS m/z calc. 446.5, found 447.5 (M+1)+; Retention time: 1.84 minutes (3 min run).

Workup

  1. washwashed with water
  2. extractionthe product was extracted into ethyl acetate
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-95bc5e1598004269b0491b5d2aab87f8
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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