Dimethylformamide → (5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol

HRID 931874Notes

Reaction equation

HRID 931874 reaction equation
Cl.[NH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].CO[C:12](OC)([CH3:14])[CH3:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CN(C)C=O>C(OCC)(=O)C.C(N(CC)CC)C>[NH2:2][C:3]1([CH2:8][OH:9])[CH2:6][O:7][C:12]([CH3:14])([CH3:13])[O:5][CH2:4]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 64952,2-DimethoxypropaneHCID 93573Tromethamine hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 300060(5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-amino-2-(hydroxymethyl)propane-1,3-diol hydrochloride (320 g, 2.03 mol), 2,2-dimethoxypropane (240 g, 2.30 mol), and p-toluenesulfonic acid monohydrate (16.2 g, 102 mmol) were combined into anhydrous dimethylformamide (1.0 L). The solution was stirred vigorously by a mechanical stirrer for 48 hours at room temperature. Triethyl amine (300 mL) and ethyl acetate (1.5 L) were added. A white precipitate formed immediately. The white salt was filtered off and the low boiling point solvents were removed by a rotary evaporator. The product, (5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol, was obtained by distillation (250 g, 76%), by 107° C./0.3 torr. 1H NMR (300 MHz, CDCl3) δ1.48 (s, 3H), 1.53 (s, 3H), 3.14 (br, 2H), 3.51 (s, 1H), 3.53 (d, 2H), 3.78 (d, 2H).

Workup

  1. customA white precipitate formed immediately
  2. filtrationThe white salt was filtered off
  3. customthe low boiling point solvents were removed by a rotary evaporator

Sources & evidence

ORD record
ord-14064230d3d9436ca32adacd53b1e1cb
Source dataset
uspto-grants-2016_03
Patent number
US09298093B2

Reaction notes

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