3,5-Dimethylbenzyl bromide → HCID 67751544, compound

HRID 2210685Notes

Reaction equation

HRID 2210685 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:8]2[C@@H:12]([OH:13])[CH2:11][CH2:10][N:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:35][C:36]1[CH:37]=[C:38]([CH:41]=[C:42]([CH3:44])[CH:43]=1)[CH2:39]Br>COCCOC>[C:19]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@H:8]2[C@@H:12]([O:13][CH2:35][C:36]3[CH:37]=[C:38]([CH3:39])[CH:41]=[C:42]([CH3:44])[CH:43]=3)[CH2:11][CH2:10][N:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1413343,5-Dimethylbenzyl bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 67751644HCID 67751644, compound

Product 1

HCID 67751544HCID 67751544, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of cis-2-(diphenylmethyl)-3-hydroxy-1-ethoxycarbonylpyrrolidine (Example 1d, 1.00 g, 3.1 mmol) in ethylene glycol dimethyl ether (10.0 ml) was added 0.5M potassium bis(trimethylsilyl)amide (9.00 ml, 4.5 mmol) and stirred at room temperature for 1/2h before addition of 3,5dimethylbenzyl bromide (0.92 g, 4.5 mmol) in ethylene glycol dimethyl ether (2 ml). After stirring for 18 h the solvent was removed in vacuo and the residue partitioned between water/dichloromethane. The organic phase was washed with saturated brine and dried (MgSO4). The residue, after removal of solvent in vacuo, was chromatographed on silica gel using ethyl acetate/hexane (2:3) as eluant to give cis-2-(diphenylmethyl)-3-(3,5-dimethylbenzyloxy)-1-ethoxycarbonylpyrrolidine. 1H NMR (360 MHz, DMSO-d6) δ7.05-7.46 (10H, m), 6.81 (1H, s), 6.58 (2H, s), 4.86 (1H, t, J=7.0 Hz), 4.42 (1H, d, 7.5 Hz), 4.18 (1H, d, J=12.0 Hz), 4.11 (1H, m), 3.97 (1H, d, J=12.0 Hz), 3.83 (1H, m), 3.68 (1H, m), 3.31 (1H, m), 2.98 (1H, m), 2.19 (6H, s), 2.15 (1H, m), 1.95 (1H, m), 1.03 (3H, t, J=7.0 Hz). m/z (CI+) 444 (MH).

Workup

  1. customwas removed in vacuo
  2. customthe residue partitioned between water/dichloromethane
  3. washThe organic phase was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. customThe residue, after removal of solvent in vacuo
  6. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-4130160972674ff9919644fcf4178d6a
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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