Hydride → (E)-3-(1-Ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-pent-2-en-1-ol

HRID 1582091Notes

Reaction equation

C([O:3][C:4](=O)/[C:5](/[F:26])=[C:6](\[C:9]1[CH:10]=[C:11]([CH:23]([CH3:25])[CH3:24])[CH:12]=[C:13]2[C:18]=1[N:17]([CH2:19][CH3:20])[CH2:16][CH2:15][C:14]2([CH3:22])[CH3:21])/[CH2:7][CH3:8])C.[H-]>>[CH2:19]([N:17]1[C:18]2[C:13](=[CH:12][C:11]([CH:23]([CH3:25])[CH3:24])=[CH:10][C:9]=2/[C:6](/[CH2:7][CH3:8])=[C:5](/[F:26])\[CH2:4][OH:3])[C:14]([CH3:22])([CH3:21])[CH2:15][CH2:16]1)[CH3:20]

Participants

Reactant 2

HCID 166653Hydride

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 ester2×

Product 1

HCID 69897013(E)-3-(1-Ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-pent-2-en-1-ol

Procedure

Following General Procedure F, (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 (Intermediate 16, 2.37 g, 9.08 mmol) and a 1 M solution of diisobutylalluminum hydride in hexanes (36.3 ml, 36.3 mmol) were reacted to give the title compound as light yellow oil after purification by flash chromatography (SiO2, first eluted with 5:95 ethyl acetate:hexane, followed by 1:9 ethyl acetate:hexane).

Sources & evidence

ORD record: ord-804104552b9747c891a963b5f23680a6
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734193B1

Reaction notes

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