Borane;tetrahydrofuran → 3-Hydroxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester

HRID 1872230Notes

Reaction equation

HRID 1872230 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH:14]([C:15](O)=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[C:1]([O:5][C:6]([CH:8]1[CH:14]([CH2:15][OH:16])[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 155505241-(4-Methoxy-benzenesulfonyl)-azepane-2,3-dicarboxylic acid 2-tert-butyl ester

Product 1

HCID 541061343-Hydroxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-Methoxy-benzenesulfonyl)-azepane-2,3-dicarboxylic acid 2-tert-butyl ester (1.06 g, 2.56 mmoL) in 12.8 mL THF at 0° C. was added a Borane-THF solution (1M, 6.4 mL) dropwise. The reaction was warmed to ambient temperature after 30 minutes and allowed to stir for 20 hours before cooling to ice bath temperature and carefully quenching with a 1:1 solution of acetic acid and water. This solution was stirred for 1 hour after which the majority of the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with brine. This solution was dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure and purified by column chromatography (silica: 25% to 30% ethyl acetate in hexanes) to yield 3-Hydroxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester as a clear oil; MS: (M+H)+ =400, (M+NH4)+ =417; and the cooresponding aldehyde (31 mg, 3%) as a clear oil; MS: (M+H)+ =398, (M+NH4)+ =415.

Workup

  1. temperaturebefore cooling to ice bath temperature
  2. customcarefully quenching with a 1:1 solution of acetic acid and water
  3. stirringThis solution was stirred for 1 hour after which the majority of the solvent
  4. customwas removed under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with brine
  7. dry with materialThis solution was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. custompurified by column chromatography (silica: 25% to 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6aea175be4b14a959db3663f7db4c363
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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