Hydrochloric Acid → HCID 89544929, compound

HRID 578870Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:12]2([C:15](OC)=[O:16])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[H-].C([Al+]C(C)C)(C)C.[Cl-].[NH4+].Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:12]2([CH2:15][OH:16])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

280 mg of methyl 1-[3-chloro-5-(trifluoromethyl)-2-pyridyl]cyclopropanecarboxylate (step 1) was dissolved in 5 ml of dry toluene and the solution was cooled to −78° C. under argon. 2 ml of diisopropylaluminium hydride (1.2 N in toluene) was slowly added and the solution was allowed to warm up to ambient temperature. The mixture was stirred 45 min, then cooled to 0° C. and a saturated solution of ammonium chloride was added followed by 1N hydrochloric acid. The mixture was extracted with diethyl ether, the organic phase was dried over anhydrous sodium sulphate and evaporated under reduced pressure giving an oil which solidified on standing. Thus, 220 mg of [1-[3-chloro-5-(trifluoromethyl)-2-pyridyl]cyclopropyl]methanol was obtained. 1H-NMR (CDCl3): 8.71 ppm (s, 1H), 7.92 ppm (s, 1H), 3.84 ppm (d, 2H), 1.85 ppm (t, 1H), 1.12 ppm (m, 2H), 1.07 ppm (m, 2H).

Workup

temperatureto warm up to ambient temperature
temperaturecooled to 0° C.
extractionThe mixture was extracted with diethyl ether
dry with materialthe organic phase was dried over anhydrous sodium sulphate
customevaporated under reduced pressure
customgiving an oil which

Sources & evidence

ORD record: ord-e3f14d231c0a45b6a623d2bb23fac65a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040708B2

Reaction notes

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