Methanol → 1-{2-[(7-Hydroxyheptanoyl)(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

HRID 446534Notes

Reaction equation

HRID 446534 reaction equation
[BH4-].[Li+].CO.[C:5]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]([CH3:35])[C:24](=[O:34])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](OC)=[O:31])[CH2:17][CH2:16]1)=[O:13].[OH-].[Na+]>O1CCCC1>[C:5]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:13])[O:14][CH:15]1[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][N:23]([C:24](=[O:34])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])[CH3:35])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 66794003Methyl 7-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-7-oxoheptanoate

Product 1

HCID 666716911-{2-[(7-Hydroxyheptanoyl)(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamateYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium borohydride (39 mg, 1.80 mmol) was suspended in tetrahydrofuran (6 mL), methanol (73 μL, 1.80 mmol) and a solution of the compound (235 mg, 0.450 mmol) obtained in Example 39a in tetrahydrofuran (7 mL) was added, and the mixture was stirred at room temperature for 2 days. A 1 N aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=50:1, v/v) to give the title compound (163 mg; yield, 75%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (×3)
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=50:1, v/v)

Sources & evidence

ORD record
ord-2ef87099408c4281a55109e96df16c9f
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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