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

HRID 30276Notes

Reaction equation

HRID 30276 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[CH:29]=[CH:28][S: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[CH:29]=[CH:28][S:27][C:24]=32)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3639180N-boranyl-2-methylpropan-2-amineHCID 6451240Aluminum(III) ChlorideHCID 597894175-Benzyl-3b,4,5,6,7,7a-hexahydro-3-thia-5-aza-cyclopenta[alpha]inden-8-oneHCID 178419134HCID 178419134, compound

Product 1

HCID 689045005-Benzyl-4,5,6,7,7a,8-hexahydro-3bH-3-thia-5-aza-cyclopenta[alpha]indeneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A slurry of AlCl3 (946 mg, 7.11 mmol) in CH2Cl2 (7 ml) was treated with tert-butylaminoborane (1.24 g, 14.22 mmol) at 0° C. and stirred for 30 minutes. Next, a solution of the product from step e) (671 mg, 2.37 mmol) in CH2Cl2 (5 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 in vacuo leaving the crude product that was purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (0% to 75% ethyl acetate) to give the subtitle compound (409 mg, 64%). 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 in vacuo
  7. customleaving the crude product that
  8. customwas purified by silica-gel chromatography

Sources & evidence

ORD record
ord-2f15b312e79e41948a1b98c69b5b9880
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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