2-Bromoethanol → [4-(2-Hydroxyethoxy)-2-methoxybenzyl]carbamic acid tert-butyl ester

HRID 2353602Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2].Br[CH2:20][CH2:21][OH:22]>CC(O)C.[OH-].[Na+]>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:20][CH2:21][OH:22])=[CH:11][C:10]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of (4-hydroxy-2-methoxy-benzyl)-carbamic acid tert-butyl ester (22.8 mg, 0.09 mmol) in 2-propanol (1 mL) and 2 N aq. NaOH (0.15 mL) is added 2-bromoethanol (22.5 mg, 0.18 mmol). The reaction mixture is heated to 85° C. and stirred for 8 h. The mixture is cooled to rt and subjected to prep. HPLC purification to give [4-(2-hydroxy-ethoxy)-2-methoxy-benzyl]-carbamic acid tert-butyl ester (10.3 mg) as a colourless oil. LC-MS: tR=0.85 min, [M+1]+=298.07.

Workup

temperatureThe mixture is cooled to rt
customHPLC purification

Sources & evidence

ORD record: ord-537e4b15fac44273bfa34e41ed9d749c
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750040B2

Reaction notes

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