Hydrochloric Acid → (+)-trans-1-t-Butyldimethylsilyloxymethyl-4-oxo-2-phenylcyclopentane

HRID 1357967Notes

Reaction equation

HRID 1357967 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][C:6](=[O:8])[CH2:5][C@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl>[Si:15]([O:1][CH2:2][C@@H:3]1[CH2:7][C:6](=[O:8])[CH2:5][C@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 53754795(+)-trans-3-Hydroxymethyl-4-phenylcyclopentan-1-one

Product 1

HCID 18686192(+)-trans-1-t-Butyldimethylsilyloxymethyl-4-oxo-2-phenylcyclopentaneYield 129.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+)-trans-1-hydroxymethyl-4-oxo-2-phenylcyclopentane from Example 8, Step F (3.3 g, 16 mmol) in methylene chloride (100 mL) was added t-butyldimethylsilyl chloride (11 g, 49 mmol) and DIPEA (22 mL, 74 mmol). The reaction was stirred at rt for 16 h, poured into dilute aq. HCl and extracted twice with ether. The organic layers were washed with brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FC (5% ethyl acetate in hexanes) to afford of (+)-trans-1-t-butyldimethylsilyloxymethyl-4-oxo-2-phenylcyclopentane (6.3 g) as a oil, [α]D=+97 (MeOH, c=0.2).

Workup

  1. extractionextracted twice with ether
  2. washThe organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by FC (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-574513c6ad4242279eeca5abe47a0bf7
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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