HCID 58304318, compound → HCID 58304315, compound

HRID 2424343Notes

Reaction equation

HRID 2424343 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C@:11]1([CH3:20])[C:16]2([CH2:18][CH2:17]2)[CH2:15][O:14][C:13]([NH2:19])=[N:12]1>C(O)C.CCN(CC)CC.[Pd]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C@:11]2([CH3:20])[C:16]3([CH2:17][CH2:18]3)[CH2:15][O:14][C:13]([NH2:19])=[N:12]2)[CH:4]=1

Participants

5

Reactant 1

HCID 58304318HCID 58304318, compound

Product 1

HCID 58304315HCID 58304315, compoundYield 85.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

Intermediate Fa3 (R1,2=cyclopropyl, R3=Me): A suspension of (S)-8-(2-fluoro-5-nitro-phenyl)-8-methyl-5-oxa-7-aza-spiro[2.5]oct-6-en-6-ylamine (279 mg) in ethyl alcohol (25 ml), NEt3 (0.10 ml) and Pd/C (10%, 50 mg) was hydrogenated at normal pressure and 22° C. for 1 h. The mixture was filtered, the filtrate evaporated and the residue triturated with ether to give (S)-8-(5-amino-2-fluoro-phenyl)-8-methyl-5-oxa-7-aza-spiro[2.5]oct-6-en-6-ylamine (213 mg) as a pale yellow solid. MS (ESI): m/z=250.1 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customthe residue triturated with ether

Sources & evidence

ORD record
ord-464c1cff1730458d95d15f412ba2d446
Source dataset
uspto-grants-2011_06
Patent number
US07964594B1

Reaction notes

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