Diisopropylamine → HCID 10045736, compound

HRID 1460604Notes

Reaction equation

HRID 1460604 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]1([CH2:19][O:20][CH2:21][CH:22]2[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Br:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32]Br>O1CCCC1.CCOCC>[Br:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][CH:26]1[CH2:27][CH:22]([CH2:21][O:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:23][CH2:24][C:25]1=[O:28]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 769652-Bromobenzyl bromideHCID 10443381Cyclohexanone, 4-[(phenylmethoxy)methyl]-HCID 178418339Butyllithium

Product 1

HCID 10045736HCID 10045736, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. of N,N-diisopropylamine (6.1 ml, 43.4 mmole) in dry tetrahydrofuran (50 ml) was added n-butyllithium (1.6M in hexane), (27 ml, 43.4 mmol). This solution was added slowly to a cold (-78° C.) solution of the product of Example 107. After stirring 30 minutes a solution of 2-bromobenzyl bromide (8.3 g, 33.4 mmol) was added. The mixture stirred for 6 hours at 0° C. and was poured onto water. The organics were layered with ether (500 ml). The ether layer was dried (MgSO4), concentrated in vacuo, then chromatographed to give 2.94 g (23% yield) of the title compound as a light yellow oil.

Workup

  1. additionwas added
  2. additionwas poured onto water
  3. dry with materialThe ether layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customchromatographed

Sources & evidence

ORD record
ord-21801c72d76f4f5f82c4d7a0fb99dd6c
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

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