Sodium Carbonate → HCID 67025697, compound

HRID 1951099Notes

Reaction equation

HRID 1951099 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([C:13]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:14])[CH2:10][CH:9]2[N:21]([CH3:36])[C:22](=[O:35])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([C:31]([F:34])([F:33])[F:32])[CH:24]=2)=[CH:4][CH:3]=1.C(O[BH-](O[C:47](=O)[CH3:48])OC(=O)C)(=O)C.[Na+].[C:51](=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][N:11]([C:13]([CH:15]3[CH2:20][CH2:19][N:18]([CH:47]([CH3:48])[CH3:51])[CH2:17][CH2:16]3)=[O:14])[CH2:10][CH:9]2[N:21]([CH3:36])[C:22](=[O:35])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([C:31]([F:33])([F:32])[F:34])[CH:24]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67025677HCID 67025677, compound

Product 1

HCID 67025697HCID 67025697, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[(3RS,4SR)-4-(4-chloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide (50 mg, 0.095 mmol) in dichloromethane (1 mL) was added under an atmosphere of nitrogen acetone (70 μl, 0.95 mmol) and sodium triacetoxyborohydride (81 mg, 0.38 mmol). The reaction mixture was stirred for 18 h at ambient temperature before it was treated with an aqueous solution of sodium carbonate (1 M, 10 ml) and stirred for 1 h at this temperature. It was diluted with ethyl acetate (15 mL). The aqueous layer was extracted with ethyl acetate (15 mL) and the organic layers were washed with brine (15 mL). The combined organic layers were dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, dichloromethane:methanol=100:0 to 70:30) afforded the title compound (40 mg, 73%) as a light brown oil. MS m/e: 566.3 [M]+.

Workup

  1. stirringstirred for 1 h at this temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (15 mL)
  3. washthe organic layers were washed with brine (15 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by chromatography (SiO2, dichloromethane:methanol=100:0 to 70:30)

Sources & evidence

ORD record
ord-281141e089124ff7807fb9557f00d33b
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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