Reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH3:16])[CH2:6]1)[CH2:2][CH3:3].[O:17]([CH2:24][C:25](O)=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[B-][N+](C)(C)C>CCOCC>[CH2:1]([N:4]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH3:16])[CH2:6]1)[CH2:25][CH2:24][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:2][CH3:3]Participants
Procedure
A mixture of 2-(N-n-propylamino)-5-methoxytetralin (7.0 g, 0 0319 mol; prepared according to J. Chem. Soc., 1965, pp. 26-36), phenoxyacetic acid (4.86 g, 0.0319 mol), and borane trimethylamine complex (2.33 g, 0.0319 mol) was refluxed in xylenes overnight. The cooled reaction mixture was extracted with NaHCO3 and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting oil was subjected to flash chromatography (silica; 9:1 pet ether/EtOAc) and product was isolated: NMR of the free base (300 MHz, CDCl3): δ 7.3-6.6(m, 8H), 4.0(t, 2H), 3.7(s, 3H), 3.1-2.5(m, 9H), 2.1(m, 1H), 1.7-1.4(m, 3H), 0.9(t, 3H). The free base thus isolated was converted to hydrochloride salt by the addition of dry ether-HCL.
Workup
- customprepared
- customThe cooled reaction mixture
- extractionwas extracted with NaHCO3
- dry with materialthe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customproduct was isolated
- customThe free base thus isolated
Sources & evidence
- ORD record
- ord-adb00b0532464acfa885f84695ff13dc
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05274003
Linked notes
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