Hydrochloric Acid → 2-(1-Hydroxy-2-phenethyl-4-phenyl-butyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1828066Notes

Reaction equation

HRID 1828066 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15]1([CH:21]([Mg]Br)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]([OH:14])[CH:23]([CH2:22][CH2:21][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 42278151-Boc-2-FormylpyrrolidineHCID 178419684HCID 178419684, compound

Product 1

HCID 210277702-(1-Hydroxy-2-phenethyl-4-phenyl-butyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.5 g (2.5 mmol) of 2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester in anhydrous THF (20 mL) was added 5.0 mL (2.5 mmol) of 4a, and the mixture was stirred at an ambient temperature for 16 hours. The solution was poured over a 1N solution of hydrochloric acid and was extracted with EtOAc (2×100 mL). The organic phase was washed with saturated sodium bicarbonate, dried (MgSO4) and evaporated to a clear oil which was subject to column chromatography (EtOAc/Hexanes, 1:3) to yield 0.18 g (16.7%) of 10a as a clear oil. TLC Rf=0.6 (EtOAc/Hexanes, 1:3)

Workup

  1. extractionwas extracted with EtOAc (2×100 mL)
  2. washThe organic phase was washed with saturated sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. customevaporated to a clear oil which

Sources & evidence

ORD record
ord-f835ffa62e9d40fe9c25ed6dc0dfba87
Source dataset
uspto-grants-2006_06
Patent number
US07056935B2

Reaction notes

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