2-Amino-2-methyl-1,3-propanediol → HCID 11279363, compound

HRID 1962868Notes

Reaction equation

HRID 1962868 reaction equation
[H-].[Na+].[NH2:3][C:4]([CH3:9])([CH2:7][OH:8])[CH2:5][OH:6].[Si:10](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[NH2:3][C:4]([CH3:9])([CH2:7][O:8][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 24758Sodium hydrideHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 11279363HCID 11279363, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (55% in dispersion in oil) (1.141 g) was added portion wise to a solution of 2-amino-2-methyl-propane-1,3-diol (2.50 g) in dry THF (35 ml) at 0° C. The reaction mixture was stirred at room temperature for 1 h. tert-Butyldiphenylsilyl chloride (6.54 g) in dry THF (10 ml) was added dropwise 0° C. and the reaction mixture was stirred for 17 hrs at room temperature. The reaction mixture was quenched with water (18 ml) and extracted thrice with ethyl ether. The two layers were separated and the organic layer was washed once with water and then dried over sodium sulphate, filtered and concentrated under reduced pressure to yield 8.94 g of 2-amino-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propan-1-ol as a crude product which was used as such in Stage 2 described below. 1H NMR (CDCl3) δ ppm: 7.68-7.62 (4H, m); 7.47-7.37 (6H); 3.52 (2H, dd); 3.39 (2H, dd); 1.09 (9H, s); 1.02 (3H, s).

Workup

  1. additionwas added dropwise 0° C.
  2. customThe reaction mixture was quenched with water (18 ml)
  3. extractionextracted thrice with ethyl ether
  4. customThe two layers were separated
  5. washthe organic layer was washed once with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12d70f3bffc94791a5326291451028ff
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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