Sodium Hydroxide → HCID 86640056, compound

HRID 2427285Notes

Reaction equation

HRID 2427285 reaction equation
[CH:1]([O:4][C:5](=[O:28])[NH:6][C@@H:7]1[CH2:27][C:10]2[N:11]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:12]3[CH:13]=[CH:14][C:15]([CH:18]=O)=[CH:16][C:17]=3[C:9]=2[CH2:8]1)([CH3:3])[CH3:2].[OH-].[Na+].Cl.[CH3:32][O:33][NH2:34]>CO.C(OCC)(=O)C>[CH:1]([O:4][C:5](=[O:28])[NH:6][C@@H:7]1[CH2:27][C:10]2[N:11]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:12]3[CH:13]=[CH:14][C:15]([CH:18]=[N:34][O:33][CH3:32])=[CH:16][C:17]=3[C:9]=2[CH2:8]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86640055HCID 86640055, compound

Product 1

HCID 86640056HCID 86640056, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve (S)-(7-formyl-4-pyridin-2-ylmethyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-carbamic acid isopropyl ester (181 mg, 0.48 mmol) in methanol (10 mL) and 1.0 N sodium hydroxide (2.4 ml, 2.4 mmol). Add methoxyamine hydrochloride (120 mg, 1.44 mmol) and stir at room temperature overnight. Dilute with ethyl acetate, wash with 10% potassium carbonate, dry over anhydrous sodium sulfate, filter, and concentrate. Purify the crude product on a 12 g silica gel column eluting with 30% ethyl acetate/dichloromethane to obtain the pure title compound (53 mg, 27%). LCMS 407.1 (M+1).

Workup

  1. washwash with 10% potassium carbonate
  2. dry with materialdry over anhydrous sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude product on a 12 g silica gel column
  6. washeluting with 30% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-47604c8003e042f2bf2868d1dc1b6fdc
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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