Sodium Hydroxide → (r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(hydroxyimino-methyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

HRID 545580Notes

Reaction equation

HRID 545580 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][C@@H:15]([NH:19][C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([CH:25]=O)[CH:11]=2.Cl.[NH2:31][OH:32].[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][C@@H:15]([NH:19][C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([CH:25]=[N:31][OH:32])[CH:11]=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 59161221(r)-Cyclopropanecarboxylic acid[9-(3-fluorobenzyl)-6-formyl-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

Product 1

HCID 87305657(r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(hydroxyimino-methyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amideYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine (R)-cyclopropanecarboxylic acid[9-(3-fluorobenzyl)-6-formyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-amide (Preparation 71) (1.50 g, 3.82 mmol), hydroxylamine hydrochloride (0.801 g, 11.5 mmol), and sodium hydroxide (0.23 g, 5.76 mmol) and stir under nitrogen for 1.5 h. Dilute with water and extract with EtOAc. Pass the dark residue through a pad of silica eluting with 50% EtOAc/hexanes to give 1.27 g (82%) of the title compound. MS (ES): m/z 406 (M+1).

Workup

  1. extractionextract with EtOAc

Sources & evidence

ORD record
ord-caddcfd136cd4178a3c77039e5c4a049
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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