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

HRID 545582Notes

Reaction equation

HRID 545582 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.[O:31]([NH2:33])[CH3:32].[OH-].[Na+]>>[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:33][O:31][CH3:32])[CH:11]=2

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 59161221(r)-Cyclopropanecarboxylic acid[9-(3-fluorobenzyl)-6-formyl-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

Product 1

HCID 87305428(r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(1-methoxyimino-methyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

Procedure

Prepare the title compound from (R)-cyclopropanecarboxylic acid[9-(3-fluorobenzyl)-6-formyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-amide (Preparation 71) (3.10 g, 7.94 mmol), methoxylamine hydrochloride (1.99 g, 23.8 mmol), and sodium hydroxide (0.48 g, 11.9 mmol) by essentially following procedures as described in Example 204. Purify using silica gel chromatography eluting with 10% EtOAc/CH2Cl2 to provide 1.94 g (58%) of product. mp: 200-203° C.; MS (ES) m/z 420 (M+1).

Sources & evidence

ORD record
ord-930b48ac19394997802356f00d21f9a8
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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