Potassium Hydroxide → HCID 58158373, compound

HRID 390091Notes

Reaction equation

HRID 390091 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(=O)OCC2C=CC=CC=2)[CH2:4][O:3]1.[OH-].[K+]>C(O)(C)C.C(Cl)Cl>[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][NH2:12])[CH2:4][O:3]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 76689234HCID 76689234, compound

Product 2

HCID 21705897Ammonia methanolYield 7%HCID 58158373HCID 58158373, compoundYield 185.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl ((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methylcarbamate (200 mg, 589 μmol) and potassium hydroxide (992 mg, 1.77E+04 μmol) in isopropanol (8 mL) was heated under reflux for 2 h. Silica gel was added and the mixture was concentrated to dryness, then applied to a silica gel column and eluted with 5% MeOH/CH2Cl2, then 7% 7N NH3/MeOH in CH2Cl2 to give ((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methanamine (112 mg, 545 μmol, 93% yield) as a syrup. 1H NMR δ 3.96-3.83 (3H, m); 3.70 (1H, dd, J=9.9, 11.5 Hz); 2.83-2.73 (2H, m); 2.67-2.55 (2H, m); 2.18 (3H, s); 1.89-1.77 (1H, m); 1.44 (3H, s); 1.39 (3H, s). 13C NMR (CDCl3) δ 98.8, 72.9, 62.8, 41.9, 41.4, 38.5, 29.3, 20.2, 17.3.

Workup

  1. temperatureunder reflux for 2 h
  2. additionSilica gel was added
  3. concentrationthe mixture was concentrated to dryness
  4. washeluted with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a30c5270a41d411eba058606c727842a
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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