HCID 22270443, compound → HCID 22270357, compound

HRID 30369Notes

Reaction equation

HRID 30369 reaction equation
[N:1]([CH:4]([CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:5])=[N+]=[N-]>CO.Cl.O=[Pt]=O>[NH2:1][CH:4]([CH:6]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:5]

Participants

5

Reactant 1

HCID 22270443HCID 22270443, compound

Product 1

HCID 22270357HCID 22270357, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 32 mg 2-azido-5-methyl-3-phenylhexane in 1 mL MeOH and 2 drops of 1.2 N HCl, 4 mg PtO2 was added and the solution was stirred under H2 atmosphere for 2 h. The reaction was filtered through a pad of CELITE diatomaceotis earth and the pad was rinsed with MeOH. The combined filtrate was concentrated to give the desired product. 1H NMR: (500 MHz, CDCl3): δ 0.86 (m, 6H), 0.99 (d, 3H), 1.25 (m, 1H), 1.54 (m, 1H), 1.77 (m, 1H), 2.73 (m, 1H), 3.19 (m, 1H), 7.2-7.4 (m, 5H).

Workup

  1. filtrationThe reaction was filtered through a pad of CELITE diatomaceotis earth
  2. washthe pad was rinsed with MeOH
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-1b1d88666ddd40b988a7cfd1da590596
Source dataset
uspto-grants-2008_09
Patent number
US07423067B2

Reaction notes

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