HCID 59858004, compound → 1,1-Dimethylethyl N-[6-[(4-hydroxy-3-pyrrolidinyl)methyl]-2-pyridinyl]carbamate

HRID 1671616Notes

Reaction equation

HRID 1671616 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]2[CH:19]([OH:20])[CH2:18][N:17](CC3C=CC=CC=3)[CH2:16]2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]2[CH:19]([OH:20])[CH2:18][NH:17][CH2:16]2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59858004HCID 59858004, compound

Product 1

HCID 598580021,1-Dimethylethyl N-[6-[(4-hydroxy-3-pyrrolidinyl)methyl]-2-pyridinyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of [6-(1-benzyl-4-hydroxy-pyrrolidin-3-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester I-3 (0.002 mol) and 10% Pd—C (0.7 g) in MeOH (30 mL) was stirred at 45° C. under hydrogen overnight. Then, the catalyst was removed by filtration and washed with MeOH (30 mL). The filtrate was concentrated to give II-1. Most of the product was used in the next reaction without further purification (100%). Some was purified by column chromatography (silica gel, CH2Cl2:MeOH:Et3N, 6:30:0.1) to determine NMR and mass spectrum.

Workup

  1. customThen, the catalyst was removed by filtration
  2. washwashed with MeOH (30 mL)
  3. concentrationThe filtrate was concentrated
  4. customto give II-1
  5. customMost of the product was used in the next reaction without further purification (100%)
  6. customSome was purified by column chromatography (silica gel, CH2Cl2:MeOH:Et3N, 6:30:0.1)

Sources & evidence

ORD record
ord-c90673e6ccc34583aa66d1c8fd2297cb
Source dataset
uspto-grants-2011_08
Patent number
US07994326B2

Reaction notes

Loading…