Methanol → N-(2'-Tert-butoxycarbonylbiphenyl-4-ylmethyl)-4-aminotetrahydropyran-4-carboxamide

HRID 1707413Notes

Reaction equation

HRID 1707413 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:22]([C:24]2([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[OH:31]>[Pd]>[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][NH:21][C:22]([C:24]2([NH2:29])[CH2:28][CH2:27][O:31][CH2:26][CH2:25]2)=[O:23])=[CH:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 15745368N-(2'-Tert-butoxycarbonylbiphenyl-4-ylmethyl)-1-aminocyclopentane-1-carboxamide

Product 1

HCID 19422624N-(2'-Tert-butoxycarbonylbiphenyl-4-ylmethyl)-4-aminotetrahydropyran-4-carboxamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The product obtained in step C is dissolved in 30 ml of methanol. 400 mg of 10% palladium-on-charcoal are added and the mixture is hydrogenated at atmospheric pressure. After 1 hour, the catalyst is filtered off and the filtrate is then concentrated under vacuum. The residue is chromatographed on silica using an ethyl acetate/methanol/33% aqueous ammonia mixture (99/1/0.5; v/v/v) as the eluent to give 0.93 g of the expected product in the form of a white solid.

Workup

  1. filtrationthe catalyst is filtered off
  2. concentrationthe filtrate is then concentrated under vacuum
  3. customThe residue is chromatographed on silica using an ethyl acetate/methanol/33% aqueous ammonia mixture (99/1/0.5

Sources & evidence

ORD record
ord-9f3bd32b3f0b4de9aed2a24948436867
Source dataset
uspto-grants-1994_10
Patent number
US05352788

Reaction notes

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