Benzylamine → HCID 66773807, compound

HRID 1644776Notes

Reaction equation

HRID 1644776 reaction equation
C(S(O[CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([OH:15])[C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C@@H:10]1[CH2:23]OS(CCC)(=O)=O)(=O)=O)CC.[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(O)C.CO.[OH-].[Na+]>[CH2:31]([N:38]1[CH2:23][C@@H:10]2[C@H:9]([CH2:14][CH2:13][C@H:12]([OH:15])[C@H:11]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:8]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 2

HCID 7504BenzylamineHCID 71763654HCID 71763654, compound

Product 1

HCID 66773807HCID 66773807, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
140 °C

Procedure

In a pressure tube was placed a solution of crude [(1S,2R,3R,4S)-4-hydroxy-3-(2-methylphenyl)cyclohexane-1,2-diyl]di(methylene) dipropanesulfonate (Step 1.85 g, 184 mmol) in ˜120 mL ethanol and benzylamine (70.2 mL, 643 mmol). The pressure tube was sealed and heated at 140° C. in an oil bath for 3 hr. The tube was cooled to RT and opened. LC-MS showed that the reaction was completed. The resulting mixture was diluted with 180 mL methanol and 100 mL 5 N aq. NaOH. The ethanol, some of water and benzylamine were removed under vacuum. The residue was dissolved in ethyl acetate and diluted with water. The organic layer was separated and the aqueous was extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and the solvent was evaporated under vacuum. The combined organics were concentrated, and the residue oil was purified by column chromatography (1:9 methanol:ethyl acetate. 1H-NMR (CDCl3): δ: 7.35-7.10 (9H, m), 3.81-3.62 (3H, m), 2.94 (1H, t, J=8.1 Hz), 2.83 (1H, t, J=10.0 Hz), 2.52 (2H, m), 2.40 (1H, t, J=10.0 Hz), 2.36 (3H, s), 2.20 (1H, m), 2.02-1.85 (3H, m), 1.60 (1H, m), 1.36 (1H, m). M++1: 322.19.

Workup

  1. customIn a pressure tube was placed
  2. customThe pressure tube was sealed
  3. temperatureThe tube was cooled to RT
  4. customThe ethanol, some of water and benzylamine were removed under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. additiondiluted with water
  7. customThe organic layer was separated
  8. extractionthe aqueous was extracted with ethyl acetate
  9. dry with materialThe combined organic layers were dried over MgSO4
  10. filtrationfiltered
  11. customthe solvent was evaporated under vacuum
  12. concentrationThe combined organics were concentrated
  13. customthe residue oil was purified by column chromatography (1:9 methanol

Sources & evidence

ORD record
ord-b182c0cf101e44748db405e105f5845a
Source dataset
uspto-grants-2012_02
Patent number
US08124633B2

Reaction notes

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