Ethanol → HCID 66902531, compound

HRID 2242306Notes

Reaction equation

HRID 2242306 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]2[CH:3]1[C@H:4]2[C:8]([OH:10])=[O:9].C(O)C.[CH2:14]([NH:21][C@@H:22]([CH3:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)(=O)C>[CH2:14]([NH:21][CH:22]([CH3:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]2[CH:3]1[C@H:4]2[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 66902185HCID 66902185, compound

Product 1

HCID 66902531HCID 66902531, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of crude (±)(6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid (11.9 g, 84.9 mmol, assume 100% potency) in 119 mL of 6:1 ethyl acetate:ethanol at reflux is added 18 g (85.1 mmol) of (S)-N-benzyl-α-methylbenzyl-amine. Upon dissolution, the mixture is allowed to cool optionally followed by seeding at 52° C. Upon cooling to room temperature and stirring an additional 13.5 h, the crystals are collected and washed with 6:1 ethyl acetate:ethanol (2×48 mL). Drying in vacuo gave 10.8 g (36%, 77% de) of the resolved salt as a solid.

Workup

  1. dissolutionUpon dissolution
  2. temperatureto cool optionally
  3. customby seeding at 52° C
  4. customthe crystals are collected
  5. washwashed with 6:1 ethyl acetate
  6. customDrying in vacuo

Sources & evidence

ORD record
ord-4dd2a6bcaaae43648f1b028346857eb9
Source dataset
uspto-grants-2010_03
Patent number
US07671082B2

Reaction notes

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