Triethylamine → HCID 14676874, compound

HRID 1165581Notes

Reaction equation

HRID 1165581 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]1[C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]=2[S:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[C:24]([O:28][C:29](ON=C(C1C=CC=CC=1)C#N)=[O:30])([CH3:27])([CH3:26])[CH3:25]>O1CCCC1>[CH3:1][N:2]([CH2:3][CH:4]1[C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]=2[S:7][CH2:6][CH2:5]1)[C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 14676871HCID 14676871, compound

Product 1

HCID 14676874HCID 14676874, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-methylaminomethyl-2,3,4,5-tetrahydrothiopyrano[3,2-b]indole (5.47 g) in dry tetrahydrofuran (50 ml) is mixed with triethylamine (3.58 g) and 2-t-butoxycarbonyloxyimino-2-phenylacetonitrile (5.93 g), allowed to stand at room temperature for 4 hours and evaporated to dryness. The residue is dissolved in methylene chloride and washed with a dilute sodium hydroxide solution. The solution is washed with water, dried and evaporated to dryness. The residue is applied to column chromatography on silica gel eluted with benzene/ether (20:1) to give 4-(N-methyl-N-t-butoxycarbonylaminomethyl)-2,3,4,5-tetrahydrothiopyrano[ 3,2-b]indole (5.33 g): Yield 68.2%. Recrystallization from benzene/petroleum benzine gives crystals melting at 151°-153° C. (decomp.).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue is dissolved in methylene chloride
  3. washwashed with a dilute sodium hydroxide solution
  4. washThe solution is washed with water
  5. customdried
  6. customevaporated to dryness
  7. washeluted with benzene/ether (20:1)

Sources & evidence

ORD record
ord-aab327aa47214b3ea4dbbc7296952986
Source dataset
uspto-grants-1990_03
Patent number
US04910318

Reaction notes

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