5',5'-dimethyl-3-nitro-6,8,9,10-tetrahydro-5H-spiro[cycloocta[b]pyridine-7,2'-[1,3]dioxane] → HCID 59295549, compound

HRID 252906Notes

Reaction equation

HRID 252906 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:7][O:6][C:5]2([CH2:21][CH2:20][CH2:19][C:11]3=[N:12][CH:13]=[C:14]([N+:16]([O-])=O)[CH:15]=[C:10]3[CH2:9][CH2:8]2)[O:4][CH2:3]1>C(O)C.C1COCC1.[Pd]>[CH3:1][C:2]1([CH3:22])[CH2:7][O:6][C:5]2([CH2:21][CH2:20][CH2:19][C:11]3=[N:12][CH:13]=[C:14]([NH2:16])[CH:15]=[C:10]3[CH2:9][CH2:8]2)[O:4][CH2:3]1

Participants

4

Reactant 1

HCID 592956745',5'-dimethyl-3-nitro-6,8,9,10-tetrahydro-5H-spiro[cycloocta[b]pyridine-7,2'-[1,3]dioxane]

Product 1

HCID 59295549HCID 59295549, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The compound of formula (Cc), 5′,5′-dimethyl-3-nitro-6,8,9,10-tetrahydro-5H-spiro[cycloocta[b]pyridine-7,2′-[1,3]dioxane], was hydrogenated in ethanol/THF solution over 10% Pd/C for 1 hour at 40 psi to give the compound of formula (Cd), 5′,5′-dimethyl-6,8,9,10-tetrahydro-5H-spiro[cycloocta[b]pyridine-7,2′-[1,3]dioxan]-3-amine, in quantitative yield; MS (ES) 277.67 (M+2H).

Sources & evidence

ORD record
ord-7e0b8fa7dd2c44b89a7b847a2a37195a
Source dataset
uspto-grants-2011_01
Patent number
US07872000B2

Reaction notes

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