Phenethylamine → (2S,3R)-3-(3-Phenethylamino-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid ethyl ester

HRID 2196834Notes

Reaction equation

HRID 2196834 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@H:10]([CH2:11][CH2:12][CH:13]=O)[CH2:9][CH2:8][N:7]1[C@@H:15]([CH3:22])/[C:16](/[CH3:21])=[CH:17]/[CH:18]=[CH:19]\[CH3:20])=[O:5])[CH3:2].[CH2:23]([NH2:31])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[BH3-]C#N.[Na+]>CCO.CCOCC>[CH2:1]([O:3][C:4]([C@@H:6]1[C@H:10]([CH2:11][CH2:12][CH2:13][NH:31][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:9][CH2:8][N:7]1[C@H:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:22])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 5003444Sodium cyanoborohydrideHCID 86601083(2S,3R)-1-((2E,4Z)-(S)-1,2-Dimethyl-hexa-2,4-dienyl)-3-(3-oxo-propyl) pyrrolidine-2-carboxylic acid ethyl ester

Product 1

HCID 67004170(2S,3R)-3-(3-Phenethylamino-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid ethyl esterYield 30.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (2S,3R)-1-((2E,4Z)—(S)-1,2-Dimethyl-hexa-2,4-dienyl)-3-(3-oxo-propyl)pyrrolidine-2-carboxylic acid ethyl ester (1 g, crude) in EtOH (10 mL) is added phenethylamine (0.44 g, 3.65 mmol) at r.t. After stirring at r.t. for 30 min, NaBH3CN (0.3 g, 4.87 mmol) is added in one portion, After stirring at r.t. for 1.5 Hrs, the reaction solution is diluted with 50 mL of ether and washed with 20 mL of brine. The ether layer is concentrated and the crude product is purified by chromatography (CH2Cl2/MeOH: 97/3) to give a pale liquid (405 mg, 30.0%). (NMR and MS data confirmed, U-4117-52-20).

Workup

  1. stirringAfter stirring at r.t. for 1.5 Hrs
  2. washwashed with 20 mL of brine
  3. concentrationThe ether layer is concentrated
  4. customthe crude product is purified by chromatography (CH2Cl2/MeOH: 97/3)

Sources & evidence

ORD record
ord-b84812c800224adeb8fa847a8041cabe
Source dataset
uspto-grants-2012_12
Patent number
US08338440B2

Reaction notes

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