Sodium borohydride → HCID 86586509, compound

HRID 1350159Notes

Reaction equation

HRID 1350159 reaction equation
[CH:1]([O:4][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][C@H:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:20][O:19][C:11]3=2)[N:6]=1)([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)(C(F)(F)F)=O>[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:17])([F:16])[F:18])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]3[N:22]([CH2:13][C:15]([F:18])([F:17])[F:16])[C@H:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:20][O:19][C:11]3=2)[N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69317141HCID 69317141, compound

Product 1

HCID 86586509HCID 86586509, compoundYield 169.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

This compound was prepared according to General Method 6 (EXAMPLE 3) from (3R)-3,4-dihydro-8-isopropoxy-3-phenyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (49.5 mg, 0.127 mmol) and NaBH4 (300 mg, 7.9 mmol) in 5 mL TFA, to afford 50.7 mg (85%) of (3R)-3,4-dihydro-8-isopropoxy-3-phenyl-4-(2,2,2-trifluoroethyl)-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline, a yellow solid, after column chromatography (1:3 CH2Cl2:hexanes). 1H NMR (400 MHz, CDCl3) δ 7.55–7.10 (m, 8H), 5.50 (septet, 1H, J=6.2), 4,77 (dd, 1H, J=4.4, 3.4), 4.39 (dd, 1H, J=11.0, 3.4), 4.29 (dd, 1H, J=11.0, 4.4), 4.10 (m, 1H), 3.66 (m, 1H), 1.40 (d, 6H, J=6.2).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-a85a1f812afa4655830643dbb28cacca
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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