Isoamylamine → HCID 18646604, compound

HRID 1030655Notes

Reaction equation

HRID 1030655 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11](Cl)[C@H:10]1[OH:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:26])[CH2:22][CH:23]([CH3:25])[CH3:24].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:21]([NH:26][C@H:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:18][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:10]1[OH:20])[CH2:22][CH:23]([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 7894IsoamylamineHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22843613HCID 22843613, compound

Product 1

HCID 18646604HCID 18646604, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon a solution of (1R,2S,3R)-3-tert-butoxycarbonylamino-1-chloro-1,2,3,4-tetrahydro-2-naphthalenol (BOC-amino-cis-chlorohydrin) (500 mg) in anhydrous tetrahydrofuran was refluxed with isoamylamine (1.0 ml) and triethylamine (250 μl ) for 5 hours at 90° C. The mixture was poured in aqueous 5% sodium bicarbonate and extracted with methylene chloride. The organic solution was dried over magnesium sulfate and evaporated under vacuum to yield an oil. Crystallization of this oil in hexane yielded the title compound as a white solid (270 mg).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. customevaporated under vacuum
  4. customto yield an oil
  5. customCrystallization of this oil in hexane

Sources & evidence

ORD record
ord-b9974c5c7fe5468f817288c09d92cfd8
Source dataset
uspto-grants-1992_04
Patent number
US05106861

Reaction notes

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