tert-Butyldimethylsilyl chloride → HCID 86682896, compound

HRID 2368908Notes

Reaction equation

HRID 2368908 reaction equation
[N:1]1([C@@H:5]([CH3:8])[CH2:6][OH:7])[CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]([Si:13](Cl)([CH3:15])[CH3:14])([CH3:12])[CH3:11]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[Si:13]([O:7][CH2:6][C@@H:5]([N:1]1[CH2:4][CH2:3][CH2:2]1)[CH3:8])([C:10]([CH3:12])([CH3:11])[CH3:9])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 86682897HCID 86682897, compound

Product 1

HCID 86682896HCID 86682896, compoundYield 12.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of (S)-2-(azetidin-1-yl)propan-1-ol (99.7 mmol), TBSCl (15.8 g, 105 mmol), DMAP (1.22 g, 10 mmol), and TEA (30.3 g, 0.30 mol) in toluene (150 mL) was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was purified on a silica gel column eluted with a 1:5 ethyl acetate/petroleum ether then a 1:10 MeOH/DCM, to afford the title compound (2.92 g). 1H NMR (CDCl3): δ 3.54-3.49 (m, 1H), 3.29-3.16 (m, 5H), 2.33-2.27 (m, 1H), 2.07-1.98 (m, 2H), 0.88 (s, 9H), 0.87 (d, 3H), 0.03 (s, 6H); LCMS: 230 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified on a silica gel column
  3. washeluted with a 1:5 ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-f92d9992e2f841ea80ff234380bc0cc6
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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