Sodium borohydride → HCID 21094348, compound

HRID 1350153Notes

Reaction equation

HRID 1350153 reaction equation
C(O[C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]3[NH:22][CH:21]([CH2:23][CH2:24][CH3:25])[CH2:20][O:19][C:11]3=2)[N:6]=1)(C)C.[BH4-].[Na+]>FC(F)(F)C(O)=O>[CH2:23]([CH:21]1[CH2:20][O:19][C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[C:10]2[N:22]1[CH2:13][C:15]([F:18])([F:17])[F:16])[NH:6][CH2:5][CH:14]=[C:13]3[C:15]([F:18])([F:17])[F:16])[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21094351HCID 21094351, compound

Product 1

HCID 21094348HCID 21094348, compoundYield 284%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 119 was prepared according to General Method 6 (EXAMPLE 3) from (±)-3,4-dihydro-8-isopropoxy-3-propyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (16 mg, 0.05 mmol) and NaBH4 pellets (>10 equiv) in 11 mL trifluoroacetic acid (0.04 M) stirred at rt for 12 h to afford 27 mg of (+)-3,4-dihydro-3-propyl-4-(2,2,2-trifluoroethyl)-10-(trifluoromethyl)-8H-[1,4]oxazino[2,3-f]quinoline. This material (27 mg, 0.06 mmol) was carried on according to General Method 4 (EXAMPLE 1) by treatment with 1:1 acetic acid:concentrated HCl (0.03M) and heated at 90° C. for 6 h to afford 11 mg (50% for the 2 steps) of Compound 119 after flash chromatography (3:1 hexanes:EtOAc to 1:1 hexanes:EtOAc, gradient elution). 1H NMR (500 MHz, CDCl3) δ 11.78 (bs, 1H), 7.14 (s, 1H), 7.07 (d, J=8.8, 1H), 6.95 (d, J=8.8, 1H), 4.35 (dd, J=10.7, 1.5, 1H), 3.99 (dd, J=10.7, 2.4, 1H), 3.83 (m, 1H), 3.72 (m, 1H), 3.32 (m, 1H), 1.51 (m, 2H), 1.42 (m, 2H), 0.93 (t, J=7.3, 3H).

Sources & evidence

ORD record
ord-a19333d67f644a7db26c35aa2354cc8d
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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