Sodium borohydride → HCID 54182718, compound

HRID 2268609Notes

Reaction equation

HRID 2268609 reaction equation
[C:1]([O:5][C:6](=[O:34])[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([C:23](=[O:32])[N:24]([CH2:28][CH2:29][C:30]#[N:31])[CH:25]([CH3:27])[CH3:26])[CH:20]=[C:19]([Cl:33])[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[C:1]([O:5][C:6](=[O:34])[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([Cl:33])[CH:20]=[C:21]([C:23](=[O:32])[N:24]([CH2:28][CH2:29][CH2:30][NH2:31])[CH:25]([CH3:26])[CH3:27])[CH:22]=1)[C:8]1[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 54281942HCID 54281942, compound

Product 1

HCID 54182718HCID 54182718, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Procedure

A solution of (2-{3-chloro-5-[(-cyano-ethyl)-isopropyl-carbamoyl]-phenoxy}-ethyl)-pyridin-4yl-carbamic acid tert-butyl ester (0.200 g) in methanol (2 ml) at 0° C. was treated with cobalt (II) chloride hexahydrate (0.195 g) and sodium borohydride (0.078 g) and stirred overnight at room temperature. Silica was added and the mixture was evaporated under reduced pressure, the residue was subjected to flash chromatography eluting with methanol:chloroform:ammonia(0.88) (10:89:1 v/v/v). The required fractions were evaporated under reduced pressure to give the title compound as a pale straw coloured oil (0.128 g).

Workup

  1. additionSilica was added
  2. customthe mixture was evaporated under reduced pressure
  3. washeluting with methanol:chloroform:ammonia(0.88) (10:89:1 v/v/v)
  4. customThe required fractions were evaporated under reduced pressure

Sources & evidence

ORD record
ord-39bad163831c4dbeb2feac7251ea3f52
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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