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

HRID 2223511Notes

Reaction equation

HRID 2223511 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-80e3e2087207476aa6025bd7f116aae5
Source dataset
uspto-grants-2008_05
Patent number
US07375134B2

Reaction notes

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