Dichloromethane → {[(2S)-2-amino-4-methylpentyl]oxy}(tert-butyl)dimethylsilane

HRID 1620906Notes

Reaction equation

HRID 1620906 reaction equation
ClCCl.[NH2:4][C@H:5]([CH2:10][OH:11])[CH2:6][CH:7]([CH3:9])[CH3:8].C(N(CC)CC)C.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C1C=CN=CC=1)C.O>[Si:19]([O:11][CH2:10][C@@H:5]([NH2:4])[CH2:6][CH:7]([CH3:9])[CH3:8])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 111307L-Leucinol

Product 1

HCID 11345273{[(2S)-2-amino-4-methylpentyl]oxy}(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

To a room temperature dichloromethane (100 mL) solution of L-leucinol (6.0 g) was added triethylamine (11 mL), DMAP (0.1 g) and t-butyldimethylsilyl chloride (8.5 g). The mixture was stirred at room temperature for 2 hours and then water was added. The organic layer was separated and the aqueous further extracted with dichloromethane. The combined organic layers were washed with brine, dried with magnesium sulfate and the solvent was removed in vacuo to yield the title compound, a residue which was used as such in the next reaction. 1H NMR (CD3COCD3) δ 3.48 (m, 2H), 3.32 (m, 1H), 2.76 (m, 1H), 1.78 (m, 1H), 1.22-1.02 (m, 2H), 0.88 (m, 15H), 0.06 (s, 6H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous further extracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-390795ab339042a2aa5ff6572f4b1a6f
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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