Diisopropylamine → HCID 131717858, compound

HRID 1590409Notes

Reaction equation

HRID 1590409 reaction equation
C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].[CH2:9]([Li])CCC.C(NC(C)C)(C)C.C([CH:23]([CH2:35][CH3:36])[C:24]([NH:26]P(O)(OCC(C)C)=O)=[O:25])C.[F:37]/[C:38](=[CH:42]\[C@@H:43]1[CH2:45][C@H:44]1[C:46]1[CH:51]=[CH:50][C:49]([Cl:52])=[C:48]([Cl:53])[CH:47]=1)/C(=O)C>O1CCCC1.O>[CH2:6]([NH:26][C:24](=[O:25])/[CH:23]=[C:35](\[CH3:36])/[C:38](/[F:37])=[CH:42]/[C@@H:43]1[CH2:45][C@H:44]1[C:46]1[CH:51]=[CH:50][C:49]([Cl:52])=[C:48]([Cl:53])[CH:47]=1)[CH:5]([CH3:7])[CH3:9]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 18651187HCID 18651187, compoundHCID 131717859HCID 131717859, compoundHCID 178418339Butyllithium

Product 1

HCID 131717858HCID 131717858, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium diisopropylamide in tetrahydrofuran under nitrogen, prepared from n.butyl lithium (2.3 ml) and diisopropylamine (0.51 ml), at -70° was treated with diethyl-N-isobutylphosphonoacetamide (0.46 g) in dry tetrahydrofuran. After 2 hours at 25° the above ketone (0.5 g) was added. After 18 hours at 25° water was added and the mixture worked up in the normal manner. Purification by chromatography (silica. ether/hexane) gave the title compound (0.24 g).

Workup

  1. customPurification by chromatography (silica. ether/hexane)

Sources & evidence

ORD record
ord-9dc856f7a3b94f3e8b6fc6839a7b3f8f
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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