Allyl bromide → HCID 131724978, compound

HRID 1070581Notes

Reaction equation

HRID 1070581 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 131724979HCID 131724979, compoundHCID 178418400CID 536281002×

Product 1

HCID 131724978HCID 131724978, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 13181,10-PhenanthrolineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-8-methyl-chroman-7-yl]-carbamic acid tert-butyl ester (0.41 g, 1.0 mmole) in anhydrous tetrahydrofuran (20 mL) containing 0.010 g 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. After an additional 4 hours the reaction was quenched with water (4 mL). The reaction mixture was 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% ethyl acetate/hexane) afforded 0.38 g (85%) of the title compound as an oil, [M+H]+: 448, [α]25D=+34.0° (c=1.03, THF).

Workup

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

Sources & evidence

ORD record
ord-9fef7edbcde34d918e341274563e5108
Source dataset
uspto-grants-2005_06
Patent number
US06903110B2

Reaction notes

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