Potassium Hydroxide → (R)-5-(3-(benzyloxycarbonylamino)piperidin-1-yl)-8-cyano-9H-carbazole-2-carboxylic acid

HRID 1811097Notes

Reaction equation

HRID 1811097 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]3[C:19]=2[C:20]2[CH:21]=[CH:22][C:23]([C:33]([O:35]CC)=[O:34])=[CH:24][C:25]=2[NH:26]3)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]3[C:19]=2[C:20]2[CH:21]=[CH:22][C:23]([C:33]([OH:35])=[O:34])=[CH:24][C:25]=2[NH:26]3)[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86642946(R)-ethyl 5-(3-(benzyloxycarbonylamino)piperidin-1-yl)-8-cyano-9H-carbazole-2-carboxylate

Product 1

HCID 66605842(R)-5-(3-(benzyloxycarbonylamino)piperidin-1-yl)-8-cyano-9H-carbazole-2-carboxylic acidYield 21%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Step 3 A solution of (R)-ethyl 5-(3-(benzyloxycarbonylamino)piperidin-1-yl)-8-cyano-9H-carbazole-2-carboxylate (0.67 g, 1.349 mmol) and potassium hydroxide (0.379 g, 6.75 mmol) in 10:1 ethanol-water (33 mL) was heated at 85° C. for 2 h. The mixture was cooled to rt and the precipitate was collected by filtration, washed with ethanol and dried to afford (R)-5-(3-(benzyloxycarbonylamino)piperidin-1-yl)-8-cyano-9H-carbazole-2-carboxylic acid as a yellow solid (130 mg, 21%). Mass spectrum m/z 469.1 (M+H)+. (R)-5-(3-aminopiperidin-1-yl)-8-cyano-9H-carbazole-2-carboxylic acid was also isolated from filtrates (150 mg, 33%). Mass spectrum m/z 335.2 (M+H)+.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-86af763977ce4beda674e5bec4521d90
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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