Allyl bromide → HCID 131724980, compound

HRID 1070586Notes

Reaction equation

HRID 1070586 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[C:17]([CH3:18])=[C:16]2[C:11]([CH2:12][CH2:13][C@H:14]([C:19]([CH3:27])([CH3:26])[O:20][SiH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[O:15]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:29]([Li])([CH2:31]C)[CH3:30].C(Br)C=C>O1CCCC1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[C:17]([CH2:18][CH2:31][CH:29]=[CH2:30])=[C:16]2[C:11]([CH2:12][CH2:13][C@H:14]([C:19]([CH3:27])([CH3:26])[O:20][SiH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[O:15]2)=[CH:10][CH:9]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 131724981HCID 131724981, compoundHCID 178418400CID 536281002×

Product 1

HCID 131724980HCID 131724980, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 13181,10-PhenanthrolineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-8-methyl-chroman-7-yl]-carbamic acid tert-butyl ester (0.41 g, 1 mmole) in anhydrous tetrahydrofuran (20 mL) containing 10 mg of 1,10-phenanthroline at −40° C. was slowly added 2.4 equivalents of 1.3 M s-butyl lithium. After 1 equivalent of s-butyl lithium had been added, the deep red color of the indicator became apparent. The reaction was allowed to stand for 1.5 hours, after which allyl bromide (0.24 g, 2.0 mmole) was added. The reaction was allowed to stand for an additional 4 hours and then was quenched with water (4 mL). The reaction mixture was next diluted with ether (250 mL) and washed with saturated aqueous sodium bicarbonate (50 mL). The organic layer was separated and the solvent removed under vacuum. Column chromatography on silica gel (5% methylene chloride/hexane) afforded 0.37 g (75%) of the title compound as an oil, [α]25D=−32.42° (3.7, THF).

Workup

  1. waitto stand for an additional 4 hours
  2. customwas quenched with water (4 mL)
  3. additionThe reaction mixture was next diluted with ether (250 mL)
  4. washwashed with saturated aqueous sodium bicarbonate (50 mL)
  5. customThe organic layer was separated
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-27830f027e43443a85dd6af90239ab88
Source dataset
uspto-grants-2005_06
Patent number
US06903110B2

Reaction notes

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