Water → HCID 66953648, compound

HRID 390093Notes

Reaction equation

HRID 390093 reaction equation
[CH3:1][C:2]1([CH3:23])[O:7][CH:6]([CH2:8][S:9][CH3:10])[CH:5]([CH2:11][NH:12][C:13](=O)OCC2C=CC=CC=2)[CH2:4][O:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1.C(Cl)Cl.CO>[NH3:12].[CH3:2][OH:3].[CH3:1][C:2]1([CH3:23])[O:7][CH:6]([CH2:8][S:9][CH3:10])[CH:5]([CH2:11][NH:12][CH3:13])[CH2:4][O:3]1

Participants

9

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 76689234HCID 76689234, compound

Product 2

HCID 21705897Ammonia methanolYield 5%HCID 66953648HCID 66953648, compoundYield 113.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of benzyl ((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methylcarbamate (82 mg, 242 μmol) in dry THF (1.5 mL) was added lithium aluminium hydride 2.0 M in THF (1208 μl, 2416 μmol) and the solution was stirred at RT for 18 h. Then water (0.12 mL), 15% NaOH (0.12 mL) and water (0.36 mL) were added carefully. The resulting mixture was filtered, the solids were washed with warm EtOAc and the filtrate was concentrated to dryness. Chromatography (5% MeOH in CH2Cl2, then 5% 7N NH3/MeOH in CH2Cl2) gave 1-((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)-N-methylmethanamine (30 mg, 137 μmol, 56.6% yield) as a syrup. 1H. NMR (CDCl3) δ 3.94-3.80 (2H, m); 3.69-3.62 (2H, m); 2.82 (1H, dd, J=2.9, 13.8 Hz); 2.64 (1H, dd, J=6.9, 13.8 Hz); 2.55 (1H, dd, J=4.7, 12.0 Hz); 2.44-2.38 (1H, m); 2.39 (3H, s); 2.18 (3H, s); 2.01-1.90 (1H, m); 1.44 (3H, s); 1.39 (3H, s). 13C NMR (CDCl3) δ 99.1, 73.9, 63.6, 51.8, 39.5, 38.7, 37.5, 29.6, 20.3, 17.6.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe solids were washed with warm EtOAc
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-5f4017e3a42a4ffcb7128660fa66cd83
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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