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

HRID 1859049Notes

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

Participants

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

customis subsequently evaporated to dryness
washwashed with water
concentrationAfter concentrating under reduced pressure, chromatography on silica gel (dichloromethane)
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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