HCID 16659512, compound → HCID 16658990, compound

HRID 990955Notes

Reaction equation

HRID 990955 reaction equation
[CH2:1]([C@H:5]1[N:10]([CH2:11][C:12]([F:15])([F:14])[F:13])[C:9]2[CH:16]=[CH:17][C:18]([N+:20]([O-])=O)=[CH:19][C:8]=2[O:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3]>C(OCC)(=O)C.[Pd]>[NH2:20][C:18]1[CH:17]=[CH:16][C:9]2[N:10]([CH2:11][C:12]([F:15])([F:14])[F:13])[C@H:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:6][O:7][C:8]=2[CH:19]=1

Participants

4

Reactant 1

HCID 16659512HCID 16659512, compound

Product 1

HCID 16658990HCID 16658990, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared according to General Method 4 (EXAMPLE 1) from (3R)-3,4-dihydro-3-isobutyl-7-nitro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine (0.22 g, 0.69 mmol) and 10% Pd/C (0.075 g) in 5 mL ethyl acetate to afford 0.13 g (65%) of (3R)-7-amino-3,4-dihydro-3-isobutyl-4-trifluoroethyl-2H-1,4-benzoxazine. Data for (3R)-7-amino-3,4-dihydro-3-isobutyl-4-trifluoroethyl-2H-1,4-benzoxazine: Rf 0.3 (3:1 hexanes:EtOAc); 1H NMR (400 MHz, CDCl3) δ 6.63 (d, 1H, J=8.5), 6.27 (dd, 1H, J=8.5, 2.6), 6.23 (d, 1H, J=2.5), 4.10 (dd, 1H, ABx, J=10.6, 1.8), 3.97 (dd, 1H, ABx, J=10.6, 2.3), 3.70-3.51 (m, 2H), 3.38 (broad s, 2H), 3.19-3.13 (m, 1H), 1.75-1.63 (m, 1H), 1.47-1.25 (m, 2H), 0.93 (d, 3H, J=6.6), 0.89 (d, 3H, J=6.6).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-e043cd3e964348b099230bcd27a2f29b
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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