tert-Butyldimethylsilyl chloride → HCID 66784101, compound

HRID 1096813Notes

Reaction equation

HRID 1096813 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][OH:9])[N:3]=[CH:2]1.CCN(C(C)C)C(C)C.[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:23]([O:9][CH2:8][CH2:7][CH2:6][C:4]1[N:3]=[CH:2][S:1][CH:5]=1)([C:20]([CH3:22])([CH3:21])[CH3:19])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 147742743-(1,3-Thiazol-4-yl)propan-1-ol

Product 1

HCID 66784101HCID 66784101, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A sol. of 3-thiazol-4-yl-propan-1-ol (610 mg, 4.26 mmol), DIPEA (1.82 mL, 10.7 mmol), DMAP (catalytic amount) and TBDMS-Cl (964 mg, 6.40 mmol) in CH2Cl2 (12 mL) was stirred at rt for 1 h. The mixture was diluted with more CH2Cl2, and washed with aq. 1M HCl, aq. sat. NaHCO3, and brine. The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:9→2:8→1:1) yielded the title compound (996 mg, 91%). LC-MS: tR=1.06, ES+: 258.18.

Workup

  1. washwashed with aq. 1M HCl, aq. sat. NaHCO3, and brine
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (EtOAc/heptane 1:9→2:8→1:1)

Sources & evidence

ORD record
ord-645364b9ef374362b64324cf9eb741f8
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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