Sodium Hydroxide → HCID 69654803, compound

HRID 1243998Notes

Reaction equation

HRID 1243998 reaction equation
C(O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[C:8](O)(=O)[CH2:9][C:10](O)=[O:11].[C:15]1([C@H:21]2[C@@H:26]([NH2:27])[CH2:25][CH2:24][CH2:23][NH:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:28][O:29][C:30]1[CH:38]=[C:37]2[C:33]([CH2:34][C:35](=[O:40])[N:36]2[CH3:39])=[CH:32][C:31]=1[CH:41]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.O>[CH3:8][CH2:9][O:5][C:3]([CH3:2])=[O:4].[CH3:10][OH:11].[NH4+:22].[OH-:29].[CH3:28][O:29][C:30]1[CH:38]=[C:37]2[C:33]([CH2:34][C:35](=[O:40])[N:36]2[CH3:39])=[CH:32][C:31]=1[CH2:41][NH:27][C@H:26]1[CH2:25][CH2:24][CH2:23][NH:22][C@H:21]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 21931790HCID 21931790, compoundHCID 86587882HCID 86587882, compound

Product 2

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 69654803HCID 69654803, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a slurry of added (2S,3S)-2-Phenyl-piperidin-3-ylamine dimalonate (1.26 g, 2.6 mmol) and 6-Methoxy-1-methyl-2-oxo-2,3-dihydro-1H-indole-5-carbaldehyde in 15 mL CH2Cl2 was added sodium triacetoxyborohydride (1.01 g, 4.8 mmol) in one portion. After 30 minutes the mixture was diluted with 10 mL of water and then basified with 3 N NaOH to a pH of ca. 11. The layers were separated and the aqueous portion was extracted once with CH2Cl2. The combined organic material was washed successively with 1 N NaOH and water, and was then dried with Na2SO4 and concentrated. Silica gel chromatography (90:9:1 EtOAc/MeOH/NH4OH) gave 127 mg (14%) of the title compound as a white solid. Mass spectrum m/e calcd for M+H=366.2. Found 366.0. The solid dihydrochloride salt was generated by treatment with excess HCl in ether followed by concentration in vacuo.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous portion was extracted once with CH2Cl2
  3. washThe combined organic material was washed successively with 1 N NaOH and water
  4. dry with materialwas then dried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-945095f2af4c49cdb605809fb5575502
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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