Diethyl Ether → HCID 69285596, compound

HRID 2225310Notes

Reaction equation

HRID 2225310 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=O)OC(C)(C)C)[CH2:14][C@H:13]1[C:26]1[O:30][N:29]=[C:28]([CH3:31])[N:27]=1)=O)C1C=CC=CC=1.Br.[CH3:33][C:34](O)=O.[CH3:37]COCC>>[CH:34]([N:18]([CH3:19])[C@@H:15]1[CH2:16][CH2:17][C@H:12]([NH2:11])[C@H:13]([C:26]2[O:30][N:29]=[C:28]([CH3:31])[N:27]=2)[CH2:14]1)([CH3:33])[CH3:37]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86596976HCID 86596976, compound

Product 1

HCID 69285596HCID 69285596, compound

Procedure

The entirety of benzyl (1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(3-methyl-1,2,4-oxadiazol-5-yl)cyclohexylcarbamate prepared in Step 2 (270 mg, 0.7 mmol) was charged with 30% HBr/AcOH (5 mL). The reaction vessel warms and a vigorous gas evolution occurs. The mixture was stirred for 25 min at RT and then the flask was placed in a cool water bath before the addition of 20 mL of Et2O. The resulting solid was collected, washed with Et2O twice, and concentrated in vacuo to give (1R,3R,4S)-N1-isopropyl-N1-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)cyclohexane-1,4-diamine (250 mg). MS found: (M+H)+=253.

Workup

  1. customThe resulting solid was collected
  2. washwashed with Et2O twice
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c1a85c5220341278213c5671b21c29f
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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