Hydrochloric Acid → Rac-(cis)-3-phenylpyrrolidin-2-ylmethanol

HRID 2075368Notes

Reaction equation

HRID 2075368 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:9]1[CH2:19][OH:20])=O)(C)(C)C.C1COCC1.Cl.[OH-].[Na+]>CO>[C:13]1([C@H:10]2[CH2:11][CH2:12][NH:8][C@H:9]2[CH2:19][OH:20])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68973925Rac-(cis)-tert-butyl-2-(hydroxymethyl)-3-phenylpyrrolidine-1-carboxylate

Product 1

HCID 98008479Rac-(cis)-3-phenylpyrrolidin-2-ylmethanolYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

rac-(cis)-3-Phenylpyrrolidin-2-yl)methanol. To a stirred solution of rac-(cis)-tert-butyl-2-(hydroxymethyl)-3-phenylpyrrolidine-1-carboxylate, racemic (0.2133 g, 769 μmol) in THF (2.0 mL, 24409 μmol) was added hydrogen chloride (4.0 N solution in 1,4-dioxane) (1.9 mL, 7690 μmol) at room temperature. The resulting mixture was stirred at room temperature for 1 hour. The entire mixture was neutralized with SN NaOH and concentrated to give rac-(cis)-3-phenylpyrrolidin-2-ylmethanol (76 mg, 56% yield) as a white solid, which was pure enough to be used without further purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-353d24fec09448a2be83a27412f29c6a
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

Loading…