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Sodium borohydride → 3-{Benzyl-[2-(2-bromophenyl)-2-hydroxyethyl]amino}propanenitrile

HRID 1859049
Notes
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Reaction equation

HRID 1859049 reaction equation
[CH2:1]([N:8]([CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Br:22])=[O:15])[CH2:9][CH2:10][C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]([CH2:13][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Br:22])[OH:15])[CH2:9][CH2:10][C:11]#[N:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 221232153-{Benzyl-[2-(2-bromophenyl)-2-oxoethyl]amino}propanenitrile

Product 1

HCID 221232233-{Benzyl-[2-(2-bromophenyl)-2-hydroxyethyl]amino}propanenitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

The 131.9 g of product obtained in Step 1 are dissolved in 300 ml of methanol and then added dropwise to 39.9 g of sodium borohydride in 300 ml of methanol. The temperature is maintained at 0° C. throughout the period of addition; the reaction mixture is then left at ambient temperature overnight and is subsequently evaporated to dryness, taken up in dichloromethane and washed with water. After concentrating under reduced pressure, chromatography on silica gel (dichloromethane) allows 94 g of expected product to be isolated.

Workup

  1. customis subsequently evaporated to dryness
  2. washwashed with water
  3. concentrationAfter concentrating under reduced pressure, chromatography on silica gel (dichloromethane)
  4. customto be isolated

Sources & evidence

ORD record
ord-3c3f85b4aa6949cbb964093407922ed4
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06153640

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes