Triethylamine → 3-Hydroxymethyl-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid tert butyl ester

HRID 1872245Notes

Reaction equation

HRID 1872245 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH:14]([C:15](O)=[O:16])[CH2:13][CH:12]=[CH: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].C(N(CC)CC)C.ClC(OCC(C)C)=O>C1COCC1>[C:1]([O:5][C:6]([CH:8]1[CH:14]([CH2:15][OH:16])[CH2:13][CH:12]=[CH: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

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 155505231-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester

Product 1

HCID 538968433-Hydroxymethyl-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid tert butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester (1.17 g, 2.65 mmoL) in 26.5 mL THF at 0° C. was added triethylamine (0.406 mL, 2.915 mmoL) followed by isobutyl chloroformate (0.378 mL, 2.915 mmoL). This suspention was allowed to stir for one hour. The suspention was then filtered into a dropping funnel which was added dropwise to a previously prepared sodium borohydride (321 mg, 8,48 mmoL) solution in 1.63 mL of water at 0° C. After 2.5 hours the solvent was stripped and the residue was diluted with ethyl acetate and water. The solution was washed once with 0.5N HCL, the layers separated, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (silica: 25% to 35% ethyl acetate in hexanes) to yield 3-Hydroxymethyl-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid tert butyl ester; MS: (M+H)+ =398, (M+NH4)+ =415.

Workup

  1. filtrationThe suspention was then filtered into a dropping funnel which
  2. additionwas added dropwise to a previously prepared sodium borohydride (321 mg, 8,48 mmoL) solution in 1.63 mL of water at 0° C
  3. waitAfter 2.5 hours the solvent was stripped
  4. additionthe residue was diluted with ethyl acetate and water
  5. washThe solution was washed once with 0.5N HCL
  6. customthe layers separated
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by column chromatography (silica: 25% to 35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7bf6de5b12364b24b9701d753fd04638
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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