HCID 59846403, compound → HCID 40787227, compound

HRID 1363231Notes

Reaction equation

HRID 1363231 reaction equation
[N:1]([C@H:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)=[N+]=[N-]>CO.[Pd]>[F:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][CH2:5][C@H:4]2[NH2:1])=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 59846403HCID 59846403, compound

Product 1

HCID 40787227HCID 40787227, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(R)-1-azido-7-fluoro-1,2,3,4-tetrahydronaphthalene (4.85 g) was dissolved in methanol (70 mL) and mixed with Pd/C (10%, wet, 485 mg), applied to Parr apparatus under H2 (35 psi) overnight. The catalyst was removed by filtration and washed twice with MeOH. The filtrate and washings were combined and evaporated under reduced pressure to give a yellow oil product (3.82 g, 91%). 1H NMR (400 MHz, DMSO-d6) δ 7.28 (dd, 1H), 7.06 (t, 1H), 6.91 (m, 1H), 3.74-3.76 (m, 1H), 2.60-2.72 (m, 2H), 2.10 (broad, 2H), 1.80-1.90 (m, 2H), 1.45-1.67 (m, 2H). 19F NMR (400 MHz, DMSO-d6) δ −117.6.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed twice with MeOH
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e3d9c84916db4ec2861d3eec890b3b95
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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