Acetic Acid → HCID 22499233, compound

HRID 2401600Notes

Reaction equation

HRID 2401600 reaction equation
C(N(CC)CC)C.[CH2:8]1[C:12]2=[CH:13][C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=3[CH:20]=[C:11]2[CH2:10][CH:9]1[NH2:21].[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.ClCCl>[CH2:22]([NH:21][CH:9]1[CH2:10][C:11]2=[CH:20][C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=[C:12]2[CH2:8]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 224991882,3,5,6,7,8-Hexahydro-1H-benz[f]inden-2-amine

Product 1

HCID 22499233HCID 22499233, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

According to the procedure of A. F. Abdel-Magid, et. al. J. Org. Chem. 1996, 61, 3849-3862. triethylamine (0.87 mL, 6.17 mmol) is added to a stirred suspension 2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-2-ylamine in 1,2-dichloroethane (30 mL) under nitrogen at room temperature. Benzaldehyde (0.52 mL, 5.14 mmol) is then added followed by sodium triacetoxyborohydride (1.64 g, 7.7 mmol) and acetic acid (0.44 mL, 7.7 mmol). The reaction is stirred at room temperature for 18 hours. After diluting with dichloromethane the mixture is washed with aqueous NaOH (50 mL, 1M) followed by brine. Removal of the solvent and chromatography (silica, ethyl acetate/hexane, 2:1) affords an oil.

Workup

  1. washis washed with aqueous NaOH (50 mL, 1M)
  2. customRemoval of the solvent and chromatography (silica, ethyl acetate/hexane, 2:1)
  3. customaffords an oil

Sources & evidence

ORD record
ord-8f221b3cfef448caa5d3f7374a91e31a
Source dataset
uspto-grants-2014_08
Patent number
US08796307B2

Reaction notes

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