(R)-(-)-Tetrahydrofurfurylamine → HCID 58612211, compound

HRID 2105297Notes

Reaction equation

HRID 2105297 reaction equation
C(N)[C@@H]1OCCC1.[N+:8]([C:11]1[CH:24]=[CH:23][C:14]([CH2:15][NH:16][CH2:17][C@H:18]2[CH2:22][CH2:21][CH2:20][O:19]2)=[CH:13][CH:12]=1)([O-])=O>C(OCC)(=O)C.[Rh]>[O:19]1[CH2:20][CH2:21][CH2:22][C@@H:18]1[CH2:17][NH:16][CH2:15][C:14]1[CH:13]=[CH:12][C:11]([NH2:8])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 2734124(R)-(-)-TetrahydrofurfurylamineHCID 26580537HCID 26580537, compound

Product 1

HCID 58612211HCID 58612211, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Using the procedure of Example 1, (R)-(−)-tetrahydrofurfurylamine Compound 40a was used in place of piperidine to prepare (4-nitro-benzyl)-[(2R)-tetrahydro-furan-2-ylmethyl]-amine Compound 40b. 5% Rh/C (1.5 g) was added to a solution of Compound 40b (5.95 g, 25.2 mmol) in ethyl acetate (40 mL). The mixture was hydrogenated at 40 psi for a period of 2 hrs, then filtered through Celite. The filtrate was evaporated in vacuo to provide 4-({[(2R)-tetrahydro-furan-2-ylmethyl]-amino}-methyl)-phenylamine Compound 40c. MS 207 (MH+). Using the procedure of Example 1, Compound 40c was used in place of 4-piperidin-1-ylmethyl-phenylamine Compound 1k to provide Compound 17. MS 553, 555 (MH+).

Workup

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-fd29d2af121a4331bd50130d155f8f59
Source dataset
uspto-grants-2009_08
Patent number
US07579356B2

Reaction notes

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