1-Phenethylamine, (+)- → (1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylate.(R)-1-phenylethanamine

HRID 1969572Notes

Reaction equation

HRID 1969572 reaction equation
[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:9]1[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[CH:11]([CH3:17])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1([C@H:31]([NH2:33])[CH3:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[CH2:18]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]1[CH2:13][C@H:12]([C:14]([O-:16])=[O:15])[C@H:11]([CH3:17])[CH2:10]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1.[C:25]1([C@H:31]([NH2:33])[CH3:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 585575354-(Dibenzylamino)-2-methylcyclopentanecarboxylic acid

Product 1

HCID 86761815(1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylate.(R)-1-phenylethanamineYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(dibenzylamino)-2-methylcyclopentanecarboxylic acid (1240 g, 1499 mmol, prepared using X with Example #24 Step H and dibenzylamine and TT) in THF (8.0 L) was added (R)-(+)-1-phenylethylamine (0.193 L, 1499 mmol). The mixture was warmed to reflux to dissolve the solids, and was then cooled to ambient temperature. After about 15 h, the reaction mixture was filtered, washed THF (800 mL) and dried in a vacuum oven to afford (1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylate•(R)-1-phenylethanamine (565 g, 85%, 97.5% ee): LC/MS (Table 2, Method 70) Rt=8.49 min. The mother liquor was concd. The residue was dissolved in THF (1 L), heated to dissolve the solids, and cooled to ambient temperature. After about 15 h, the reaction mixture was filtered, washed THF (800 mL) and dried in a vacuum oven to afford additional (1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylate•(R)-1-phenylethanamine (78.5 g, 12%, 95.2% ee): HPLC (Table 2, Method 70) Rt=8.57 min

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux
  3. dissolutionto dissolve the solids
  4. filtrationthe reaction mixture was filtered
  5. washwashed THF (800 mL)
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-47ad20ab1da24d94991f3cc8aabe2508
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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