Sodium Hydroxide → 4-Pyrrolidin-1-ylmethyl-piperidine-1-carboxylic Acid Tert-butyl Ester

HRID 1179346Notes

Reaction equation

HRID 1179346 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 589780244-Pyrrolidin-1-ylmethyl-piperidine-1-carboxylic Acid Tert-butyl EsterYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 2 (2.0 g) in DCM (40 mL) was added pyrrolidine (1.0 g) followed by sodium triacetoxyborohydride (2.8 g). The resulting mixture was stirred overnight, and treated with 10% NaOH (20 mL). The resulting mixture was extracted with DCM (300 mL). The combined extracts were washed with water (50 mL) and brine (50 mL), dried (MgSO4), and concentrated under reduced pressure to give the title compound as a light pink-brown oil (2.4 g).

Workup

  1. extractionThe resulting mixture was extracted with DCM (300 mL)
  2. washThe combined extracts were washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-300c1478b43140ff9496c00669de598e
Source dataset
uspto-grants-2007_10
Patent number
US07279491B2

Reaction notes

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