Imidazole → HCID 59060801, compound

HRID 47683Notes

Reaction equation

HRID 47683 reaction equation
Br.[CH2:2]([N:9]([CH2:21][C@H:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([Br:32])[CH:28]=2)[O:23]1)[CH2:10][C@H:11]([OH:20])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CN=C1.[Si:38](Cl)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39]>ClCCl>[Br:32][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[O:23][C@@H:22]([CH2:21][N:9]([CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:10][C@H:11]([O:20][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:31][CH2:30]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 69894008(2s)-1-(Benzyl{[(2r)-6-bromo-3,4-dihydro-2h-chromen-2-yl]methyl}amino)-3-phenoxy-2-propanol hydrobromide

Product 1

HCID 59060801HCID 59060801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 86 (5.0 g, 10.4 mmol) and imidazole (1.06 g, 15.6 mmol, 1.5 eq.) were dissolved in dichloromethane. tert-Butyldimethylsilylchloride (2.03 g, 13.5 mmol, 1,3 eq.) was added, and the mixture was stirred for 15 hours. Solids were removed by filtration, and the filtrate was concentrated in vacuo. The resulting oil was purified by flash chromatography on silica gel eluted with 90:10 hexanes/ethyl acetate. The title compound was obtained as a yellow oil (5.3 g, 85%): 1H NMR (300 MHz, CDCl3) δ7.30-7.26 (m, 5 H), 7.25-7.20 (m, 3 H), 7.09 (s, 1 H), 6.91 (t, 1 H), 6.80 (d, 2 H), 6.63 (d, 1 H), 4.07-4.00 (m, 2 H), 3.81 (s, 2 H), 3.73 (dd, 1 H), 2.88-2.77 (m, 2 H), 2.64-2.56 (m, 4 H), 1.96-1.90 (m, 1 H), 1.61-1.55 (m, 1 H), 0.85 (s, 9 H), 0.07 (s, 3 H), 0.04 (s, 3 H); MS m/z 596.3 (MH+).

Workup

  1. customSolids were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting oil was purified by flash chromatography on silica gel
  4. washeluted with 90:10 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-e6c32866b9944e7686944ba15ca55ad9
Source dataset
uspto-grants-2004_03
Patent number
US06699860B2

Reaction notes

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