Water → HCID 66853665, compound

HRID 1162320Notes

Reaction equation

HRID 1162320 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][C:23]2[N:24]=[C:25]([CH:36]=[O:37])[N:26]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:27]=2)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[C:17]([O:16][C:15](=[O:21])[N:14]([CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1)[CH2:22][C:23]1[N:24]=[C:25]([CH2:36][OH:37])[N:26]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:27]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86609872HCID 86609872, compound

Product 1

HCID 66853665HCID 66853665, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl (1-benzyl-4-piperidinyl)((2-formyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)methyl)carbamate (1.3 g) obtained in Example 83d) in ethanol (10 ml) was added sodium borohydride (95 mg) at 0° C., and mixed at room temperature for 1 hour. Water (1 ml) was added thereto, the solvent was then distilled off under reduced pressure, and the residue was diluted with ethyl acetate and water. The organic layer was collected by separation, washed with saturated brine and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain the title compound as a colorless oil (1.3 g, 98%).

Workup

  1. additionmixed at room temperature for 1 hour
  2. distillationthe solvent was then distilled off under reduced pressure
  3. additionthe residue was diluted with ethyl acetate and water
  4. customThe organic layer was collected by separation
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-04871b34dfc74ce08aef7fb9e56eadac
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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