Ethanol → Tert-butyl 4-(benzyloxy)pyridin-2-ylcarbamate

HRID 240550Notes

Reaction equation

HRID 240550 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([OH:18])C.[CH3:19][C:20]([OH:23])([CH3:22])[CH3:21]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:18])[O:23][C:20]([CH3:22])([CH3:21])[CH3:19])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6386tert-ButanolHCID 5200844-(Benzyloxy)pyridin-2-amine

Product 1

HCID 66937350Tert-butyl 4-(benzyloxy)pyridin-2-ylcarbamateYield 85%

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(benzyloxy)pyridin-2-amine (4.6 g, 22.97 mmol) in tBuOH (50 mL) was added boc-anhydride (5.57 g, 25.5 mmol). After heating to 50° C. for 1 hour, ethanol (200 mL) was added to the reaction mixture. The room temperature mixture was filtered to provide the solid product (5.89 g, 85%).

Workup

  1. filtrationThe room temperature mixture was filtered

Sources & evidence

ORD record
ord-85d68bf845744d2ba7074bbf124f2b57
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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