Chloroform → benzyl (RS)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropylcarbamate

HRID 390087Notes

Reaction equation

HRID 390087 reaction equation
C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[OH:16][CH:17]1[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20][CH2:19][CH:18]1[CH2:26][NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(Cl)(Cl)Cl.CCOC(C)=O>CC(C)=O>[CH3:25][C:21]1([CH3:24])[O:20][CH:19]([CH:18]([CH2:17][OH:16])[CH2:26][NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:23][O:22]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 131730260HCID 131730260, compound

Product 1

HCID 76741568benzyl (RS)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropylcarbamateYield 47%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Camphorsulfonic acid (0.069 g, 0.296 mmol) was added to a solution of benzyl ((5R/S,6R/S)-6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)methylcarbamate (1.83 g, 5.92 mmol) in acetone (50 mL) and the solution was stirred at RT. After 40 mins chloroform was added and the solution was washed with aq NaHCO3 and then processed normally. Chromatography (EtOAc/Hex 1:1, and then 3:1) gave firstly benzyl (RS)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropylcarbamate (0.86 g, 2.78 mmol, 47.0% yield) and then benzyl ((4RS,5RS)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methylcarbamate (0.942 g, 3.05 mmol, 51.5% yield) as syrups; compound 10.3 13C NMR (CDCl3) δ 157.6, 136.8, 128.9, 128.6, 128.5, 109.3, 76.4, 68.0, 67.3, 61.3, 44.3, 39.9, 26.9, 25.7; compound 10.4 13C NMR (CDCl3) δ 157.1, 136.8, 128.9, 128.6, 128.5, 99.0, 72.5, 69.1, 67.3, 64.2, 62.3, 40.3, 36.7, 29.1, 20.2.

Workup

  1. washthe solution was washed with aq NaHCO3

Sources & evidence

ORD record
ord-bf2bd51fa33349b182c4bc8569b69510
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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