Triethylamine → HCID 69150601, compound

HRID 1373156Notes

Reaction equation

HRID 1373156 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-5976e7e4958e41e78f623beaafeb1163
Source dataset
uspto-grants-2007_01
Patent number
US07160907B2

Reaction notes

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