Sodium Bicarbonate → HCID 70667981, compound

HRID 2407659Notes

Reaction equation

HRID 2407659 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.C(=O)(O)[O-].[Na+]>C(#N)C.C(O)(=O)C>[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:16][CH2:15]3)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 113672673-Phenyl-1,2-oxazole-5-carbaldehydeHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)

Product 1

HCID 70667981HCID 70667981, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of the compound prepared in Example 7 (2.00 g), tert-butyl piperidin-4-ylmethylcarbamate (2.72 g) and acetic acid (0.66 mL) in acetonitrile (60 mL) was stirred at room temperature for 30 minutes. Tetramethylammonium triacetoxyborohydride (9.12 g) was added and the reaction was stirred overnight. The reaction was then poured into a saturated aqueous sodium bicarbonate solution and the resulting mixture was extracted three times with ethyl acetate. The combined organics were dried with anhydrous magnesium sulfate and concentrated to a white solid. The solid was triturated with hexane to obtain the title compound (3.90 g) having the following physical data.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. dry with materialThe combined organics were dried with anhydrous magnesium sulfate
  3. concentrationconcentrated to a white solid
  4. customThe solid was triturated with hexane

Sources & evidence

ORD record
ord-c483293dcd164048becde7f92d66eaf8
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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