1,1-Dimethylethyl (2R)-2-[2-(4-methyl-1-piperidinyl)ethyl]-1-pyrrolidinecarboxylate → HCID 54041338, compound

HRID 1386022Notes

Reaction equation

HRID 1386022 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2C(OC(C)(C)C)=O)[CH2:4][CH2:3]1>FC(F)(F)C(O)=O.ClCCl>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][NH:11]2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 107090751,1-Dimethylethyl (2R)-2-[2-(4-methyl-1-piperidinyl)ethyl]-1-pyrrolidinecarboxylate

Product 1

HCID 54041338HCID 54041338, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the protected amine, (R)-2-[2-(4-methyl-piperidin-1-yl)ethyl ]pyrrolidine-1-carboxylic acid, tert-butyl ester (D5) (3.0 g, 10 mmol) in trifluoroacetic acid (15 ml) and dichloromethane (50 ml) was heated to reflux for 18 hours. The reaction mixture was concentrated and the residue partitioned between CH2Cl2 and sat. aqueous K2CO3. The organic phase was dried and concentrated to afford the title compound (2.0 g, q) MH+ 197.

Workup

  1. temperatureto reflux for 18 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue partitioned between CH2Cl2 and sat. aqueous K2CO3
  4. customThe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6d766e5fd2214577a1c990c70076b4fe
Source dataset
uspto-grants-2001_07
Patent number
US06265408B1

Reaction notes

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