Sodium Bicarbonate → 1-[[(6RS)-6-(N-tert-Butoxycarbonylaminomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl]methyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine

HRID 352839Notes

Reaction equation

HRID 352839 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:20]O)[CH:16]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.FC(F)(F)C(O)=O.[Cl:40][C:41]1[CH:42]=[C:43]2[C:48](=[CH:49][CH:50]=1)[CH:47]=[C:46]([S:51]([N:54]1[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]1)(=[O:53])=[O:52])[CH:45]=[CH:44]2.C(=O)(O)[O-].[Na+]>ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([CH2:20][N:57]3[CH2:56][CH2:55][N:54]([S:51]([C:46]4[CH:45]=[CH:44][C:43]5[C:48](=[CH:49][CH:50]=[C:41]([Cl:40])[CH:42]=5)[CH:47]=4)(=[O:53])=[O:52])[CH2:59][CH2:58]3)[CH:14]=[CH:13][C:12]=2[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 22709613Tert-butyl ((6-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-2-YL)methyl)carbamateHCID 22710058HCID 22710058, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 227099231-[[(6RS)-6-(N-tert-Butoxycarbonylaminomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl]methyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

In dichloromethane (5 ml), the (2RS)-2-(N-tert -butoxycarbonylaminomethyl)-6-hydroxymethyl-1,2,3,4-tetrahydronaphthalene (0.19 g) was dissolved. Pyridinium chlorochromate (0.17 g) was added to the resulting solution, followed by stirring at room temperature for 2 hours. The reaction mixture was purified as it was by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby a colorless solid (0.16 g) was obtained. The resulting solid was dissolved in dichloromethane (8 ml), followed by the addition of 1-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine trifluoroacetate (0.24 g), triethylamine (80.0 μl) and sodium triacetoxyboron hydride (0.17 g). The resulting mixture was stirred at room temperature for 16 hours under an argon gas atmosphere. An aqueous solution of sodium bicarbonate was added to the reaction mixture. The resulting mixture was diluted with dichloromethane to separate the organic layer. The organic layer was dried over sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1), whereby a colorless viscous liquid (0.33 g, 86%) was obtained.

Workup

  1. customThe reaction mixture was purified as it
  2. customwas obtained
  3. stirringThe resulting mixture was stirred at room temperature for 16 hours under an argon gas atmosphere
  4. customto separate the organic layer
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1), whereby a colorless viscous liquid (0.33 g, 86%)
  9. customwas obtained

Sources & evidence

ORD record
ord-152a82ff36c54c968a59156ff6695911
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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