tert-Butyldimethylsilyl chloride → HCID 22959074, compound

HRID 2303685Notes

Reaction equation

HRID 2303685 reaction equation
O[C:2]([C:4]([F:7])(F)F)=O.O[C:9]([C:11](F)(F)F)=[O:10].CS(C1C=CC(CN2[CH:28]=[C:27]([CH:29]3[CH2:34][CH2:33]NC[CH2:30]3)[C:26]([CH2:35]C)=N2)=CC=1)(=O)=O.CCN(C(C)C)C(C)C.[Si:48](Cl)([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49].C(=O)(O)[O-:57].[Na+]>C(Cl)Cl>[Si:48]([O:57][CH2:33][C@@H:34]1[CH2:11][C:9](=[O:10])[CH2:30][C@H:29]1[C:27]1[CH:26]=[CH:35][CH:2]=[C:4]([F:7])[CH:28]=1)([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49]

Participants

6

Reactant 4

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 131723147HCID 131723147, compound

Product 1

HCID 22959074HCID 22959074, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentan-1-one from Step D (6.23 g, 29.9 mmol) in methylene chloride (100 mL) was added DIPEA (16.0 mL, 11.6 g, 89.7 mmol) and t-butyldimethylsilyl chloride (6.80 g, 44.8 mmol). The reaction mixture was stirred at rt for 48 h, poured into aqueous sodium bicarbonate, and extracted three times with methylene chloride. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated. The residue (12 g) was purified by FC (5% ethyl acetate in hexanes) to afford the title product (8.99 g) as a oil.

Workup

  1. extractionextracted three times with methylene chloride
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue (12 g) was purified by FC (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f7f97a46efe6483abf9e9bb70dbce231
Source dataset
uspto-grants-2002_08
Patent number
US06432981B1

Reaction notes

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