HCID 57519124, compound → HCID 17861976, compound

HRID 1784456Notes

Reaction equation

HRID 1784456 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][CH2:8][CH:9]1[C:15]2[CH:16]=[CH:17][C:18]([O:20][C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[CH:19][C:14]=2[CH:13]=[CH:12][CH2:11][N:10]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])(C)(C)C>CO.[C].[Pd]>[CH3:24][N:22]([CH3:23])[C:21]([O:20][C:18]1[CH:17]=[CH:16][C:15]2[CH:9]([CH2:8][CH2:7][OH:6])[N:10]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[CH2:11][CH2:12][CH2:13][C:14]=2[CH:19]=1)=[O:25]

Participants

4

Reactant 1

HCID 57519124HCID 57519124, compound

Product 1

HCID 17861976HCID 17861976, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of t-butyl 7-dimethylcarbamoyloxy-1-(2-hydroxyethyl)-1,3-dihydro-benzo[c]azepine-2-carboxylate (207 mg, 0.550 mmol) synthesized in step (k) of Example 192 in methanol (10 ml) was added 10% palladium carbon (27 mg), and the resulting mixture was stirred for 1 hour at room temperature. After stirring, the reaction mixture was filtered through celite and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and methanol (1:1-0:1) as the eluent to afford the title compound (189 mg, yield: 91%) as a colorless oil.

Workup

  1. stirringAfter stirring
  2. filtrationthe reaction mixture was filtered through celite
  3. customevaporated in vacuo
  4. customto afford the crude product
  5. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-9834969e46d8449ab85ba9d5b530563f
Source dataset
uspto-grants-2009_03
Patent number
US07504393B2

Reaction notes

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