Dichloromethane → HCID 59343387, compound

HRID 1665869Notes

Reaction equation

HRID 1665869 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][CH2:8][C@H:9]([C@@H:11]1[CH:15]=[CH:14][CH2:13][O:12]1)[OH:10].[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ClCCl>O.O1CCCC1>[O:12]1[CH2:13][CH:14]=[CH:15][C@H:11]1[C@H:9]([OH:10])[CH2:8][NH:7][C:24](=[O:25])[O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 55281149(R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol

Product 1

HCID 59343387HCID 59343387, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium carbonate (12.26 g, 115.7 mmol) in water (80 mL) was added whilst stirring to a solution of (R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol (assumed to be 55 mmol) in tetrahydrofuran (100 mL). The mixture was cooled to 0° C. then benzylchloroformate (9.69 mL, 68.87 mmol) was added. The mixture was stirred at 0° C. for 45 minutes, then dichloromethane (400 mL) and water (400 mL) added. The organic phase was separated and the aqueous reextracted with dichloromethane (2×400 mL). The organic layer was washed with brine (400 mL), then dried (Na2SO4), filtered and reduced in vacuo to leave a residue. Flash chromatography over silica, eluting with ethyl acetate:heptane mixtures 0:100 to 65:35 gave alcohol (18) (11.58 g, 80%) as a pale yellow oil.

Workup

  1. customThe organic phase was separated
  2. washThe organic layer was washed with brine (400 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customto leave a residue
  6. washFlash chromatography over silica, eluting with ethyl acetate

Sources & evidence

ORD record
ord-0fb4397a4f9e487789d3d9acf09b1c97
Source dataset
uspto-grants-2011_10
Patent number
US08039641B2

Reaction notes

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