Sodium hydride → HCID 19049372, compound

HRID 1780034Notes

Reaction equation

HRID 1780034 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:27][C:28]1[CH:29]=[C:30]([CH:33]=[C:34]([CH3:36])[CH:35]=1)[CH2:31]Br>O1CCCC1.CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:10][O:11][CH2:27][C:28]1[CH:29]=[C:30]([CH3:31])[CH:33]=[C:34]([CH3:36])[CH:35]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1413343,5-Dimethylbenzyl bromideHCID 4066083HCID 4066083, compound

Product 1

HCID 19049372HCID 19049372, compoundYield 27.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-t-butoxycarbonylamino-3,3-diphenylpropan-1-ol (1.0 g, Example 1d) in tetrahydrofuran (5 ml) and dimethylformamide (1 ml) was added sodium hydride (0.11 g, 80% suspension in oil) over 15 minutes. After an additional 10 minutes 3,5-dimethylbenzyI bromide (0.73 g) was added and the solution stirred at room temperature for 3 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. After washing the organic phase with saturated brine and drying (MgSO4), the solvent was removed in vacuo and the residue chromatographed on silica gel in ethyl acetate/hexane (1:10) to give 2-t-butoxycarbonylamino-1-((3,5-dimethylphenyl)methyloxy)-3,3-diphenylpropane 0.38 g. 1H NMR (360 MHz, CDCl3) δ7.3-6.9 (13H, m), 4.7 (1H, bd), 4.6 (1H, bt), 4.43 (1H, d, J=16.7 Hz), 4.3 (2H, m), 3.4 (1H, dd), 3.2 (1H, dd, J=9.4 Hz and 2.82 Hz), 2.3 (6H, s), 1.3 (9H, s). m/z (CI+) 446 (M+H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washAfter washing the organic phase with saturated brine
  4. dry with materialdrying (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customthe residue chromatographed on silica gel in ethyl acetate/hexane (1:10)

Sources & evidence

ORD record
ord-884e2867d1df4fd8b5c91e1c820f5338
Source dataset
uspto-grants-1997_05
Patent number
US05629347

Reaction notes

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