Sodium borohydride → 1-[2-(3,4,5-Trimethoxyphenyl)-2-hydroxyethyl]-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidine

HRID 67061Notes

Reaction equation

HRID 67061 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[C:6]([CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[O:17][C:16]2=[O:25])[CH2:11][CH2:10]1)=[O:7].[BH4-].[Na+]>CO>[CH3:32][O:31][C:27]1[CH:26]=[C:5]([CH:6]([OH:7])[CH2:8][N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[CH2:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[O:17][C:16]3=[O:25])[CH2:13][CH2:14]2)[CH:4]=[C:3]([O:2][CH3:1])[C:28]=1[O:29][CH3:30]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 130521721-(3,4,5-trimethoxybenzoylmethyl)-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidine

Product 1

HCID 130521731-[2-(3,4,5-Trimethoxyphenyl)-2-hydroxyethyl]-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidineYield 62.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example, 2.8 g of 1-(3,4,5-trimethoxybenzoylmethyl)-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidine obtained in the same manner as in Example 7 is mixed with 150 ml of methanol. While this mixture is stirred at 0° to 10° C., 1.5 g of sodium borohydride is added thereto over a period of 2 hours. Then, the mixture is stirred overnight at room temperature. The mixture is further mixed with 1 g of sodium borohydride and stirred overnight. The white crystals deposited are separated by filtration, washed with methanol and water and dried to obtain 1.96 g of a crude product. The crude product is recrystallized from ethanol to obtain 1.76 g of the desired product.

Workup

  1. stirringThen, the mixture is stirred overnight at room temperature
  2. stirringstirred overnight
  3. customThe white crystals deposited are separated by filtration
  4. washwashed with methanol and water
  5. customdried
  6. customto obtain 1.96 g of a crude product
  7. customThe crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-a1cca614a58d45778a25f393e488744c
Source dataset
uspto-grants-1982_08
Patent number
US04344945

Reaction notes

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