Sodium hydride → HCID 16659512, compound

HRID 1350177Notes

Reaction equation

HRID 1350177 reaction equation
F[C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[N:4]([CH2:12][C:13]([F:16])([F:15])[F:14])[C@H:5]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:6][OH:7].[H-].[Na+]>C1COCC1>[CH2:8]([C@H:5]1[N:4]([CH2:12][C:13]([F:16])([F:15])[F:14])[C:3]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:2]=2[O:7][CH2:6]1)[CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 16658948HCID 16658948, compound

Product 1

HCID 16659512HCID 16659512, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

This compound was prepared according to the procedure described in EXAMPLE 41 (Structure 24 of Scheme V) from (2R)-2-[2-fluoro-4-nitro(2,2,2-trifluoroethyl)anilino]-4-methyl-1-pentanol (1.95 g, 5.76 mmol) in 30 mL THF and NaH (1.4 g, 35 mmol) in 25 mL THF heated at reflux for 1 hr to afford 0.87 g (50%) of (3R)-3,4-dihydro-3-isobutyl-7-nitro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine, a yellow oil. Data for (3R)-3,4-dihydro-3-isobutyl-7-nitro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine: Rf0.6 (3:1 hexanes:EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.79 (dd, 1H, J=9.1, 2.7), 7.71 (d, 1H, J=2.5), 6.72 (d, 1H, J=9.1), 4.30 (dd, 1H, ABx, J=11.0, 1.5), 4.19–4.06 (m, 1H), 4.06–4.01 (m, 1H), 3.82–3.73 (m, 1H), 3.53–3.47 (m, 1H), 1.71–1.61 (m, 2H), 1.38–1.29 (m, 1H), 0.99 (d, 3H, J=6.5), 0.96 (d, 3H, J=6.5).

Workup

  1. customThis compound was prepared
  2. temperatureheated
  3. temperatureat reflux for 1 hr

Sources & evidence

ORD record
ord-2d47749582c84cc8aa81e5891d6ffea1
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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