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

HRID 1892050Notes

Reaction equation

HRID 1892050 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 R.T. for 55′. tert-Butyldiphenylsilyl chloride (6.54 g) in dry THF (10 ml) were added dropwise at 0° C. and the reaction mixture was stirred for 17 hrs at R.T. The reaction mixture was quenched with water (18 ml) and then, extracted thrice with ethyl ether. The two layers were separated. 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 (containing minor impurities) which was used in the next step without any further purification.

Workup

  1. stirringthe reaction mixture was stirred for 17 hrs at R.T
  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-813a4c79c0dc4054a97670e79d76fa38
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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