Isoamylamine → HCID 18646604, compound

HRID 2249123Notes

Reaction equation

HRID 2249123 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-583caacd2542435b8da6c910afe4d101
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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