Diethyl Ether → HCID 11573330, compound

HRID 1822185Notes

Reaction equation

HRID 1822185 reaction equation
CC(C[Al]CC(C)C)C.[CH2:10]([N:17]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=1)[C@H:18]([C:22](OCC)=[O:23])[CH:19]([CH3:21])[CH3:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OCC)C>O>[CH2:10]([N:17]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=1)[CH:18]([CH:19]([CH3:21])[CH3:20])[CH2:22][OH:23])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 16682954DibahHCID 68983197HCID 68983197, compound

Product 1

HCID 11573330HCID 11573330, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

Dibal-H (7.08 mL, 7.08 mmol) was added as a 1.0 N solution in CH2CL2 at −78° C. to crude ethyl N-benzyl-N-(3-chloro-4-fluorophenyl)valinate (8-2, 0.322 g, 0.885 mmol). The mixture stirred for 5 h as it warmed to 23° C. Diethyl ether (40 mL) and H2O (1.2 mL) were added and mixture continued stirring for 20 min before filtering. The filtrate was concentrated and purified by reverse-phase liquid chromatography (Semi Prep YMC C-18 Reverse Phase Column 5% CH3CN/H2O to 95% CH3CN/H2O with 0.1% TFA present) to provide 2-[benzyl(3-chloro-4-fluorophenyl)amino]-3-methylbutan-1-ol (8-3) as a brown oil. 1H NMR (300 MHz, CDCl3) 7.37-7.171 (m, 5H), 6.92-6.86 (m, 2H), 6.67 (ddd, J=9.16, 3.35, 3.35 Hz, 1H), 4.45 (s, 2H), 3.91-3.87 (m, 1H), 3.68-3.55 (m, 2H), 2.04-1.92 (m, 1 μl), 1.70 (brs, 1H), 1.00 (d, J=6.72 Hz, 3H), 0.91 (d, J=6.71, 3H).

Workup

  1. stirringmixture continued stirring for 20 min
  2. filtrationbefore filtering
  3. concentrationThe filtrate was concentrated
  4. custompurified by reverse-phase liquid chromatography (Semi Prep YMC C-18 Reverse Phase Column 5% CH3CN/H2O to 95% CH3CN/H2O with 0.1% TFA present)

Sources & evidence

ORD record
ord-9c403e7e93d74431b648ce8a436dc136
Source dataset
uspto-grants-2009_10
Patent number
US07608739B2

Reaction notes

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