Sodium borohydride → Tert-butyl 2-(4-aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036690Notes

Reaction equation

HRID 2036690 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:20]=[CH:19][C:18]3[N:17]([CH3:21])[C:16]4[CH2:22][CH:23]5[NH:27][CH:26]([C:15]=4[C:14]=3[C:13]=2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:25][CH2:24]5)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CO.[Co](Cl)Cl>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:12]2[CH:20]=[CH:19][C:18]3[N:17]([CH3:21])[C:16]4[CH2:22][CH:23]5[NH:27][CH:26]([C:15]=4[C:14]=3[C:13]=2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:25][CH2:24]5)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67085455Tert-butyl 2-(4-cyanophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085186Tert-butyl 2-(4-aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 43.7%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the product of Example 30, step A (92 mg, 0.19 mmol) and cobalt(II) chloride (25 mg, 0.19 mmol) in anhydrous methanol (1.5 mL), cooled to 0° C. was treated with sodium borohydride (22 mg, 0.58 mmol). The reaction mixture was stirred at 0° C. for 2 h then quenched with water and filtered through a celite bed. The filtrate was concentrated in vacuo and extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide) to give tert-butyl 2-(4-aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (40 mg, 43%) as a light-yellow solid: ESI MS m/z 382 [M+H]+

Workup

  1. customthen quenched with water
  2. filtrationfiltered through a celite bed
  3. concentrationThe filtrate was concentrated in vacuo
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-36983bd1d21a4deeae86bb0ba91ec509
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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