4-Piperidinemethanol → HCID 52234807, compound

HRID 2407677Notes

Reaction equation

HRID 2407677 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]1([C:21]2[CH:25]=[C:24]([CH:26]=O)[O:23][N:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH:28]1[CH2:33][CH2:32][CH:31]([CH2:34][OH:35])[CH2:30][CH2:29]1>ClCCl>[C:15]1([C:21]2[CH:25]=[C:24]([CH2:26][N:28]3[CH2:33][CH2:32][CH:31]([CH2:34][OH:35])[CH2:30][CH2:29]3)[O:23][N:22]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 4207714-PiperidinemethanolHCID 5049666Sodium triacetoxyborohydrideHCID 113672673-Phenyl-1,2-oxazole-5-carbaldehyde

Product 1

HCID 52234807HCID 52234807, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium triacetoxyborohydride (12.2 g) was added portionwise to a room temperature mixture of the compound prepared in Example 7 (5.00 g) and piperidin-4-ylmethanol (4.99 g) in dichloromethane (150 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed sequentially with a saturated aqueous sodium bicarbonate solution and brine. The organics were dried over anhydrous magnesium sulfate and concentrated to obtain the crude title compound (8.05 g), which was used without further purification having the following physical data.

Workup

  1. washwashed sequentially with a saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialThe organics were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ac4271aac7e448568fa0134caf35d304
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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