Methanol → (r)-(6-Cyano-2,3,4,9-tetrahydro-1h-carbazol-3-yl)-carbamic acid benzyl ester

HRID 545561Notes

Reaction equation

HRID 545561 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[NH:10][CH:11]1[CH2:23][C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:24]#[N:25])[CH:20]=3)[NH:15][C:14]=2[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C(Cl)(Cl)Cl.CO>[CH2:1]([O:8][C:9](=[O:26])[NH:10][C@H:11]1[CH2:23][C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:24]#[N:25])[CH:20]=3)[NH:15][C:14]=2[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 57431676(6-Cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-carbamic acid benzyl ester

Product 1

HCID 57431677(r)-(6-Cyano-2,3,4,9-tetrahydro-1h-carbazol-3-yl)-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Resolve racemic (6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-carbamic acid benzyl ester (Preparation 61) (43.28 g) using preparative HPLC under the following conditions: Chiralcel OD column (8×35 cm), MeOH/0.2% dimethylethyl amine (DMEA) mobile phase at 350 ml/min flow rate with UV detection at 240 nM. Use 20 mL (666 mg) injections in 1:3 CHCl3/MeOH diluent with a runtime of 18.2 min and a stacked recycle injection (2 passes through the column to completely remove both isomers). First isomer to elute is is S isomer (21.34 g) with 98.2% ee. Second isomer to elute is R isomer (20.45 g) with 95.0% ee to give the title compound.

Workup

  1. customwith a runtime of 18.2 min
  2. customto completely remove both isomers)
  3. washFirst isomer to elute
  4. washSecond isomer to elute

Sources & evidence

ORD record
ord-193c50f93ebe4e859c2bb7cfec8de4f4
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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