HCID 86616779, compound → HCID 68803424, compound

HRID 1725637Notes

Reaction equation

HRID 1725637 reaction equation
[N:1]([CH:4]1[CH2:10][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][N:6]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:5]1=[O:21])=[N+]=[N-]>[Pd].CO>[NH2:1][CH:4]1[CH2:10][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][N:6]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:5]1=[O:21]

Participants

4

Reactant 1

HCID 86616779HCID 86616779, compound

Product 1

HCID 68803424HCID 68803424, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% palladium on carbon (30 mg) was added to a solution of 3-azido-1-(cyclopropylmethyl)-5-phenylazepan-2-one (0.3 g, 1.05 mmol) in methanol (4 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (1 atm). After 18 h, the reaction was filtered and concentrated. Purification by silica gel chromatography [100% dichloromethane→93% dichloromethane/7% (10% ammonium hydroxide/methanol)] gave the title compound (60 mg). The racemic product was resolved on a chiralpak AS (250×20 mm) column using 20% propanol/hexanes→50% propanol/hexanes (0.1% diethylamine in hexanes) to give four enantiomerically pure isomers. MS 259 (M+1).

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with nitrogen (3×)
  3. additionback-filled with hydrogen (1 atm)
  4. filtrationthe reaction was filtered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography [100% dichloromethane→93% dichloromethane/7% (10% ammonium hydroxide/methanol)]

Sources & evidence

ORD record
ord-a14c57505c774825b4adb52f664b3357
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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