Diisopropylamine → Bis(diisopropylamino)chlorophosphine

HRID 1883943Notes

Reaction equation

HRID 1883943 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[P:8]([Cl:11])(Cl)Cl>C1C=CC=CC=1>[CH:1]([N:4]([P:8]([N:4]([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])[Cl:11])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 24387Phosphorus trichloride

Product 1

HCID 2733425Bis(diisopropylamino)chlorophosphine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The synthesis shown in FIG. 2A can be carried out, for example, by adding anhydrous N,N-diisopropylamine to a solution of phosphorus trichloride in dry benzene to produce bis(N,N-diisopropylamino)chlorophosphine, and reacting it in situ with 2-(N-formyl-N-methyl) aminoethan-1-ol to produce phosphordiamidite 120 in about 73% yield. Phosphordiamidite 120 can then be reacted with a suitably protected nucleophile, such as 5′-O-(4,4′-dimethoxytrityl)-2′-deoxythymidine (Barone et al., Nucl. Acids Res., 12, 4051-4061 (1984)) to produce deoxyribonucleoside phosphoramidite 101 (FIG. 2A).

Sources & evidence

ORD record
ord-96f5a1818e4a4b4ca2624ee8a0550eec
Source dataset
uspto-grants-2004_07
Patent number
US06762298B2

Reaction notes

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