2-Bromophenol → HCID 69418362, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[C:9]([N:16]1[CH2:21][CH2:20][CH2:19][CH:18](O)[CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCOCC.O>[C:12]([O:11][C:9]([N:16]1[CH2:21][CH2:20][CH2:19][CH:18]([O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[CH2:17]1)=[O:10])([CH3:15])([CH3:13])[CH3:14]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
Ortho-bromophenol (1.72 g, 9.92 mmol) and racemic Boc-3-hydroxypiperidine (2 g, 9.92 mmol) were placed in THF (60 mL) with triphenylphosphine (3.9 g, 14.9 mmol), and the mixture was cooled to 0° C. DIAD (2.94 mL, 14.9 mmol) was added portion wise over 30 minutes, and the mixture was warmed to r.t. and stirred for about 16 hours. The mixture was diluted with ether (200 mL) and water was added (100 mL). The mixture was washed with 5N NaOH (100 mL), extracted with ether and concentrated. Ethyl acetate/hexanes was added, and the triphenylphosphine oxide was crystallized and filtered away. The residue was chromatographed on silica gel (ethyl acetate/hexanes) to afford the product (1.2 g, 34%) as a clear oil. MS found: 256.0 (M-Boc)
Workup
- temperaturethe mixture was warmed to r.t.
- additionwas added (100 mL)
- washThe mixture was washed with 5N NaOH (100 mL)
- extractionextracted with ether
- concentrationconcentrated
- additionEthyl acetate/hexanes was added
- customthe triphenylphosphine oxide was crystallized
- filtrationfiltered away
- customThe residue was chromatographed on silica gel (ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-f03264f844d64879bc4c8c6d7d27d7f8
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07186715B2
Reaction notes
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