Sodium borohydride → HCID 69316833, compound

HRID 1350156Notes

Reaction equation

HRID 1350156 reaction equation
Cl[C:2](F)(F)[CH2:3][N:4]1[C:17]2[C:8](=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[C:12]([O:18][CH:19]([CH3:21])[CH3:20])[CH:11]=[C:10]3[C:22]([F:25])([F:24])[F:23])[O:7][CH2:6][C@H:5]1[CH:26](C)C.[BH4-].[Na+]>ClC(F)(F)C(O)=O>[CH2:3]([N:4]1[C:17]2[C:8](=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[C:12]([O:18][CH:19]([CH3:21])[CH3:20])[CH:11]=[C:10]3[C:22]([F:24])([F:25])[F:23])[O:7][CH2:6][C@H:5]1[CH3:26])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21094371HCID 21094371, compound

Product 1

HCID 69316833HCID 69316833, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 66154Chlorodifluoroacetic acidSolvent

Procedure

This compound was prepared according to General Method 6 (EXAMPLE 3) from (3R)-4-(2-chloro-2,2-difluoroethyl)-3,4-dihydro-8-isopropoxy-3-isopropyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (30 mg, 0.1 mmol) and NaBH4 pellets (large excess, >10 equiv) in 3 mL chlorodifluoroacetic acid (0.03 M) stirred at rt for 12 h, to afford 22 mg (57%) of (3R)-4-ethyl-3,4-dihydro-8-isopropoxy-3-methyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline. 1H NMR (500 MHz, CDCl3) δ 7.44 (d, J=9.3, 1H), 7.30 (d, J=9.3, 1H), 7.21 (s, 1H), 5.98 (m, 1H), 5.49 (m, 1H), 4.55 (dd, J=10.7, 2.4, 1H), 3.84 (dd, J=10.7, 2.4, 1H), 3.79 (m, 1H), 3.54 (m, 1H), 2.93 (m, 1H), 1.84 (m, 1H), 1.39 (d, J=6.3, 3H), 1.38 (d, J=6.3, 3H), 1.00 (d, J=9.8, 3H), 0.99 (d, J=9.8, 3H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-648b216587e144e5b8769fa384cd6612
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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