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

HRID 2166890Notes

Reaction equation

HRID 2166890 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-678e1d8caba9427b9fa7d4f93f463b11
Source dataset
uspto-grants-1983_06
Patent number
US04390536

Reaction notes

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