3-Phenylpyrrolidine → HCID 11395433, compound

HRID 1182048Notes

Reaction equation

HRID 1182048 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]([NH2:19])=[O:18])=[CH:16][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:20]=1)=O.[C:21]1([CH:27]2[CH2:31][CH2:30][NH:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.CC(O)=O>[C:21]1([CH:27]2[CH2:31][CH2:30][N:29]([CH2:1][C:3]3[CH:4]=[CH:5][C:6]4[O:12][C:11]5[CH:13]=[CH:14][C:15]([C:17]([NH2:19])=[O:18])=[CH:16][C:10]=5[CH2:9][CH2:8][C:7]=4[CH:20]=3)[CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 31467433-PhenylpyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 58938005HCID 58938005, compound

Product 1

HCID 11395433HCID 11395433, compound

Reagents, catalysts & solvents 1

HCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

To a solution of aldehyde intermediate obtained in step 4, Example 1 (92 mg, 0.34 mmol) in THF/AcOH (6.5 mL/30 μL) add 3-phenylpyrrolidine (0.34 mmol). Stir the mixture at room temperature overnight. Add NaBH(OAc)3 (0.52 mmol) and stir at room temperature overnight. Eliminate the solvent and purify by ISCO chromatography (eluent: CHCl3/B 0-10%; B: EtOH/NH4OH 10%).

Workup

  1. custompurify by ISCO chromatography (eluent: CHCl3/B 0-10%; B: EtOH/NH4OH 10%)

Sources & evidence

ORD record
ord-1af58ab5254b452295738893cc67afdc
Source dataset
uspto-grants-2007_10
Patent number
US07288543B2

Reaction notes

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