Sodium borohydride → HCID 86611600, compound

HRID 1350160Notes

Reaction equation

HRID 1350160 reaction equation
[CH2:1]([C@@H:8]1[CH2:29][O:28][C:11]2=[C:12]3[C:17](=[CH:18][CH:19]=[C:10]2[NH:9]1)[N:16]=[C:15]([O:20][CH:21]([CH3:23])[CH3:22])[CH:14]=[C:13]3[C:24]([F:27])([F:26])[F:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)(C(F)(F)F)=O>[CH2:1]([C@@H:8]1[CH2:29][O:28][C:11]2=[C:12]3[C:17](=[CH:18][CH:19]=[C:10]2[N:9]1[CH2:13][C:24]([F:27])([F:26])[F:25])[N:16]=[C:15]([O:20][CH:21]([CH3:23])[CH3:22])[CH:14]=[C:13]3[C:24]([F:25])([F:26])[F:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69319639HCID 69319639, compound

Product 1

HCID 86611600HCID 86611600, compoundYield 190.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

This compound was prepared according to General Method 6 (EXAMPLE 3) from (3R)-3-benzyl-3,4-dihydro-8-isopropoxy-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (25.8 mg, 0.064 mmol) and NaBH4 (300 mg, 7.9 mmol) in 3 mL TFA, to afford 29.6 mg (95%) of (3R)-3-benzyl-3,4-dihydro-8-isopropoxy-4-(2,2,2-trifluoroethyl)-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline, a yellow solid, after column chromatography (1:9 EtOAc:hexane). 1H NMR (400 MHz, CDCl3) δ 7.51–7.10 (m, 8H), 5.51 (septet, 1H, J=6.2), 4,29 (d, 1H, J=10.5), 3.91 (m, 2H), 3.70–3.50 (m, 2H), 2.90 (dd, 1H, J=6.3, 13.3), 2.80 (dd, 1H, J=9.2, 13.3), 1.39 (d, 6H, J=6.2).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-68b40486caff4b0184bf57c3aa44a83b
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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