Water → 2-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-5-hydroxy-7-methyl-3,4,5,7-tetrahydro-2H-pyrrolo[3,4-f][1,2]thiazepine 1,1-dioxide

HRID 1168610Notes

Reaction equation

HRID 1168610 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:23][CH2:22][C:21](=[O:24])[C:20]4=[CH:25][N:26]([CH3:28])[CH:27]=[C:19]4[S:18]3(=[O:30])=[O:29])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:23][CH2:22][CH:21]([OH:24])[C:20]4=[CH:25][N:26]([CH3:28])[CH:27]=[C:19]4[S:18]3(=[O:30])=[O:29])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 99107952-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-7-methyl-3,4,5,7-tetrahydro-2H-pyrrolo[3,4-f][1,2]thiazepin-5-one 1,1-dioxide

Product 1

HCID 98030822-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-5-hydroxy-7-methyl-3,4,5,7-tetrahydro-2H-pyrrolo[3,4-f][1,2]thiazepine 1,1-dioxideYield 86.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 174 mg (0.4 mmol) of Compound 24 in 8 ml of ethanol, 151 mg (4 mmol) of sodium borohydride were added gradually under ice-cooled stirring. The resulting mixture was stirred under ice cooling for 1 hour and further at room temperature for 13 hours. Water (80 ml) was added to the reaction mixture. The thus-obtained mixture was stirred at room temperature for 30 minutes and then concentrated under reduced pressure. Post treatment and purification were conducted as in Example 15, whereby 151 mg of the title compound were obtained (yield: 86%).

Workup

  1. additionwere added gradually under ice-
  2. temperaturecooled
  3. stirringThe resulting mixture was stirred under ice cooling for 1 hour and further at room temperature for 13 hours
  4. stirringThe thus-obtained mixture was stirred at room temperature for 30 minutes
  5. concentrationconcentrated under reduced pressure
  6. customPost treatment and purification

Sources & evidence

ORD record
ord-a24cc4c67f7847f9ba2fbe381eeb0df3
Source dataset
uspto-grants-2003_09
Patent number
US06624314B2

Reaction notes

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