Benzyl Bromide → HCID 69428146, compound

HRID 1353172Notes

Reaction equation

HRID 1353172 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][NH:13][C:12](=[O:15])[CH:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[CH2:34]([N:13]1[CH2:14][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][CH:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]1=[O:15])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 2733832Lithium HexamethyldisilazideHCID 21101991HCID 21101991, compound

Product 1

HCID 69428146HCID 69428146, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 1D (0.403 g, 1.17 mmol) in 5 mL of THF at room temperature under argon was added (in one portion) 1.20 mL (in THF, 1.2 mmol) of 1M lithium bis(trimethylsilyl)amide and, after 5 min, 153 μL of benzyl bromide (1.29 mmol). After 15 h, additional portions of the base and alkylating agent were added as before. After 1 h more, the reaction mixture was quenched with saturated NaCl and extracted twice with EtOAc. The combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure. Purification by silica gel chromatography (7:33 EtOAc/CH2Cl2) provided the title compound (394 mg, 77%) as a colorless oil and a 61:39 mixture of diastereomers of unknown assignment. MS [M+H]+: found 435.

Workup

  1. waitAfter 15 h
  2. additionadditional portions of the base and alkylating agent were added as before
  3. waitAfter 1 h more
  4. customthe reaction mixture was quenched with saturated NaCl
  5. extractionextracted twice with EtOAc
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customPurification by silica gel chromatography (7:33 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-d87dd14a051440c2bbe5527b095e1f64
Source dataset
uspto-grants-2007_05
Patent number
US07220859B2

Reaction notes

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