Triethyl 2-fluoro-2-phosphonoacetate → (E)-3-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-pent-2-enoic acid ethyl ester

HRID 1582088Notes

Reaction equation

HRID 1582088 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].[CH2:16]([N:18]1[C:27]2[C:22](=[CH:23][C:24]([CH:32]([CH3:34])[CH3:33])=[CH:25][C:26]=2[C:28](=O)[CH2:29][CH3:30])[C:21]([CH3:36])([CH3:35])[CH2:20][CH2:19]1)[CH3:17]>>[CH2:2]([O:3][C:4](=[O:5])/[C:6](/[F:7])=[C:28](\[C:26]1[CH:25]=[C:24]([CH:32]([CH3:34])[CH3:33])[CH:23]=[C:22]2[C:27]=1[N:18]([CH2:16][CH3:17])[CH2:19][CH2:20][C:21]2([CH3:35])[CH3:36])/[CH2:29][CH3:30])[CH3:1]

Participants

3

Reactant 2

HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 227198251-(1-Ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-propan-1-one2×

Product 1

HCID 69898934(E)-3-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-pent-2-enoic acid ethyl ester

Procedure

Following General Procedure E, triethyl-2-fluoro-2-phosphonoacetate (15.1 g, 62.3 mmol) and 1-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-1-propanone (Intermediate 13, 4.48 g, 15.6 mmol) were reacted to give the title compound as bright yellow oil after purification by flash chromatography (SiO2, 2:98 ethyl acetate:hexane).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-6e2fdf441ff34f8693418e96f8f48c38
Source dataset
uspto-grants-2004_05
Patent number
US06734193B1

Reaction notes

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