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Sodium Bromide → 3-Formyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester

HRID 1872238
Notes
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Reaction equation

HRID 1872238 reaction equation
[C:1]([O:5][C:6]([C:8]1(CO)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br-].[Na+].CC1(C)N([O])C(C)(C)CCC1.[C:41](=O)(O)[O-:42].[Na+]>C1COCC1>[C:1]([O:5][C:6]([CH:8]1[CH:14]([CH:41]=[O:42])[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:16])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 54569686Hydroxymethyl-1-(4-methoxy-benzene sulfonyl)-azepane-2-carboxylic acid tert-butyl ester

Product 1

HCID 539203363-Formyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Hydroxymethyl-1-(4-methoxy-benzene sulfonyl)-azepane-2-carboxylic acid tert-butyl ester (0.5 g, 1.25 mmoL) in 1.25 mL in THF was added sodium bromide (19 mg, 0.19 mmoL). This suspention was cooled to 0° C. and TEMPO (25 mg, 5%) was added in followed by 1.41 mL of a 0.129M solution of sodium bicarbonate in Clorox bleach. The magnetic stirring was increased to obtain a biphasic solution and kept at that rate for three hours while the reaction gradually warmed to ambient temperature. The reaction was then quenched with sodium sulfite (1.26 g). After 20 minutes water and ethyl acetate were added in, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent removed under reduced pressure, and the residue was purified by column chromatography (silica: 15% to 25% ethyl acetate in hexanes) to yield 3-Formyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester; MS: (M+H)+ =398, (M+NH4)+ =415.

Workup

  1. temperaturewas increased
  2. customto obtain a biphasic solution
  3. customkept at that rate for three hours while the reaction
  4. temperaturegradually warmed to ambient temperature
  5. customThe reaction was then quenched with sodium sulfite (1.26 g)
  6. additionAfter 20 minutes water and ethyl acetate were added in, the layers
  7. customwere separated
  8. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe solvent removed under reduced pressure
  11. customthe residue was purified by column chromatography (silica: 15% to 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0f7bd8b7bae248dea45cb462be87a418
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06107291

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes