(4-Hydroxymethyl-benzyl)-(3-hydroxy-pyridin-2-ylmethyl)-carbamic acid tert-butyl ester → (4-Formyl-benzyl)-(3-hydroxy-pyridin-2-ylmethyl)-carbamic acid tert-butyl ester

HRID 747376Notes

Reaction equation

HRID 747376 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=1)[CH2:8][C:9]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]=[O:24])=[CH:21][CH:22]=1)[CH2:8][C:9]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 20764000(4-Hydroxymethyl-benzyl)-(3-hydroxy-pyridin-2-ylmethyl)-carbamic acid tert-butyl ester

Product 1

HCID 22018550(4-Formyl-benzyl)-(3-hydroxy-pyridin-2-ylmethyl)-carbamic acid tert-butyl esterYield 83%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (4-hydroxymethyl-benzyl)-(3-hydroxy-pyridin-2-ylmethyl)-carbamic acid tert-butyl ester (0.99 g, 2.9 mmol) in CH2Cl2 (14 mL) was stirred at room temperature with a suspension of 85% MnO2 (3.0 g, 29 mmol) for 15 hours. The catalyst was removed by filtration, and the filtrate was concentrated to give orange crystals (818 mg, 83%). 1H NMR (CDCl3) □ 1.44 (s, 9H), 4.54 (s, 2H), 4.61 (s, 2H), 7.17 (dd, 1H, J=8.1, 4.5 Hz), 7.26 (dd, 1H, J=8.1, 1.5 Hz), 7.37 (d, 2H, J=8.1 Hz), 7.84 (d, 2H, J=8.1 Hz), 8.03 (dd, 1H, J=4.5, 1.2 Hz), 9.55 (s, 1H), 10.00 (s, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8868d722bcc84e239b5bec24dedb499a
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Reaction notes

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