Water → HCID 86718354, compound

HRID 1518750Notes

Reaction equation

HRID 1518750 reaction equation
[C:1]([O:5][C:6](=[O:36])[N:7]([C@H:9]([C:31]1[O:32][CH:33]=[CH:34][CH:35]=1)[C@H:10]([CH3:30])[CH2:11][O:12][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CCOC(C)=O>CO>[C:1]([O:5][C:6](=[O:36])[N:7]([C@H:9]([C:31]1[O:32][CH:33]=[CH:34][CH:35]=1)[C@H:10]([CH3:30])[CH2:11][OH:12])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86718355HCID 86718355, compound

Product 1

HCID 86718354HCID 86718354, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.5.1b (20 g, 39.4 mmol) in MeOH (197 mL) was added tetrabutyl ammonium flouride (1.0 M in THF, 47.3 mL, 47.3 mmol, 1.2 equiv) at room temperature. After stirring for overnight, the reaction mixture was added water and EtOAc. The phase were separated and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/heptane) to give ((1S,2S)-1-Furan-2-yl-3-hydroxy-2-methyl-propyl)-methyl-carbamic acid tert-butyl ester (10.51 g, 99%). 1H NMR (400 MHz, CDCl3) 7.37 (s, 1H), 6.33 (s, 1H), 6.27 (br, s, 1H), 5.41 (br, s, 1H), 3.41 (br, s, 2H), 3.05 (s, 1H), 2.67 (s, 3H), 2.37 (m, 1H), 1.49 (s, 9H), 1.01 (m, 3H).

Workup

  1. customThe phase were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/heptane)

Sources & evidence

ORD record
ord-7282515b99984b978418ba3cf988e32d
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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