Hydrochloric Acid → 5-Benzyl-4,5,6,7,7a,8-hexahydro-3bH-1-thia-5-aza-cyclopenta[alpha]indene

HRID 30272Notes

Reaction equation

HRID 30272 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C(NB)(C)(C)C.[CH2:11]([N:18]1[CH2:26][CH:25]2[CH:21]([C:22](=O)[C:23]3[S:29][CH:28]=[CH:27][C:24]=32)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Al+3].[Cl-].[Cl-].[Cl-].B.Cl.[OH-].[Na+]>C(Cl)Cl>[CH2:11]([N:18]1[CH2:26][CH:25]2[CH:21]([CH2:22][C:23]3[S:29][CH:28]=[CH:27][C:24]=32)[CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3639180N-boranyl-2-methylpropan-2-amineHCID 6451240Aluminum(III) ChlorideHCID 597894415-Benzyl-3b,4,5,6,7,7a-hexahydro-1-thia-5-aza-cyclopenta[alpha]inden-8-oneHCID 178419134HCID 178419134, compound

Product 1

HCID 672051085-Benzyl-4,5,6,7,7a,8-hexahydro-3bH-1-thia-5-aza-cyclopenta[alpha]indene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A slurry of AlCl3 (1.32 g, 9.96 mmol) in CH2Cl2 (6 ml) was treated with tert-butylaminoborane (1.73 g, 19.92 mmol) at 0° C. and stirred for 30 minutes. Next, a solution of the product from step f) (941 mg, 3.32 mmol) in CH2Cl2 (3 ml) was added dropwise to the AlCl3/borane solution. After 2 hours at 0° C., the crude reaction mixture was poured into cold 10% HCl, treated with 2 M NaOH to pH 12 and extracted with CH2Cl2 (3×75 ml). The combined organic extracts were washed with brine (75 ml), dried (MgSO4) and solvent evaporated invacuo. The crude product was purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (0% to 75% ethyl acetate) to give the subtitle compound. MS calculated for C17H19NS+H 270, observed 270.

Workup

  1. waitAfter 2 hours at 0° C.
  2. customthe crude reaction mixture
  3. extractionextracted with CH2Cl2 (3×75 ml)
  4. washThe combined organic extracts were washed with brine (75 ml)
  5. dry with materialdried (MgSO4) and solvent
  6. customevaporated invacuo
  7. customThe crude product was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-801867bb5472442e96b80306f668d7ac
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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