Triethylamine → HCID 69150601, compound

HRID 2184381Notes

Reaction equation

HRID 2184381 reaction equation
Cl.N[C@H:3]1[CH2:7][O:6][CH2:5][C@@H:4]1[OH:8].C([N:11](CC)CC)C.[C:16](OC([O-])=O)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>ClCCl.CCOCC>[C:16]([C@H:3]1[CH2:7][O:6][CH:5]([NH2:11])[C@@H:4]1[OH:8])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22064466Tert-butyldicarbonateHCID 69151115(3R,4S)-4-Aminooxolan-3-ol--hydrogen chloride (1/1)

Product 1

HCID 69150601HCID 69150601, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

(3R,4S)-4-Amino-3-hydroxytetrahydrofuran hydrochloride (Scott et al, J. Org. Chem., 62, 4197 (1997); 0.75 g, 5.37 mmol) in dichloromethane (10 ml) was treated with triethylamine (0.8 ml) and t-butyl dicarbonate (1.3 g). The reaction was stirred at 20° C. for 18 h. The reaction mixture was diluted with ether (20 ml) washed with water, 5% aqueous citric acid and brine, dried and partially evaporated under reduced pressure, to give a white solid. This was collected, washed with hexane and dried under reduced pressure to give the title compound, (0.64 g, 58%). NMR (CDCl3) 1.45 (9H, s), 3.0 (1H, bs), 3.6 (1H, dd), 3.7 (1H, dd), 3.95 (1H, m), 4.1 (2H, m), 4.28 (1H, m), 4.7 (1H, bm).

Workup

  1. washwashed with water, 5% aqueous citric acid and brine
  2. customdried
  3. custompartially evaporated under reduced pressure
  4. customto give a white solid
  5. customThis was collected
  6. washwashed with hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-27df3e2477ed41b5af3ff2f8575f9a58
Source dataset
uspto-grants-2005_05
Patent number
US06900345B2

Reaction notes

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