Hydride → (E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-en-1-ol

HRID 1582092Notes

Reaction equation

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

Participants

Reactant 2

HCID 166653Hydride

HCID 69898585(E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-enoic acid ethyl ester2×

Product 1

HCID 22719834(E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-en-1-ol

Procedure

Following General Procedure F, (E)-3-(1-n-propyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-but-2-enoic acid ethyl ester (Intermediate 17, 1.43 g, 3.82 mmol) and a 1 M solution of diisobutylalluminum hydride in hexanes (15.3 ml, 15.3 mmol) were reacted to give the title compound as a 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-2bce3d373af04a36b9fed3ff2746e3c9
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734193B1

Reaction notes

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