4-Bromophenol → [(S)-2-(4-Bromo-phenoxy)-propyl]-carbamic acid tert-butyl ester
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O:13][C:14](=[O:20])[NH:15][CH2:16][C@H:17](O)[CH3:18])([CH3:12])([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1(C)C=CC=CC=1>[C:9]([O:13][C:14](=[O:20])[NH:15][CH2:16][C@@H:17]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:18])([CH3:12])([CH3:11])[CH3:10]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
4-Bromophenol (0.33 g, 1.88 mmol), ((R)-2-hydroxy-propyl)-carbamic acid tert-butyl ester (0.33 g, 1.88 mmol) and triphenylphosphine (0.74 g, 2.82 mmol) were dissolved in anhydrous toluene. A solution of di-tert-butyl azodicarboxylate (0.65 g, 2.82 mmol) in toluene (5 ml) was added slowly ensuring that the temperature did not exceed 35° C. The reaction mixture was heated to 80° C. and stirred overnight. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate and subsequently washed with 1M HCl, water, then brine and dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired product. Yield: 0.62 g, 100. LCMS method: 2, RT: 6.18 min; MI: 330-332 [M+1].
Workup
- customdid not exceed 35° C
- customThe solvent was removed in vacuo
- dissolutionthe residue was dissolved in ethyl acetate
- washsubsequently washed with 1M HCl, water
- dry with materialbrine and dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8282b7f486a342ba9ff94130afe14d82
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431596B2
Reaction notes
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