tert-Butyl 2-(1-((benzyloxy)carbonyl)-3-hydroxyazetidin-3-yl)piperidine-1-carboxylate → tert-Butyl 2-(3-hydroxyazetidin-3-yl)piperidine-1-carboxylate

HRID 605758Notes

Reaction equation

HRID 605758 reaction equation
[OH:1][C:2]1([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][N:17]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:5][N:4](C(OCC2C=CC=CC=2)=O)[CH2:3]1>CO.[Pd]>[OH:1][C:2]1([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][N:17]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:3][NH:4][CH2:5]1

Participants

4

Reactant 1

HCID 59469243tert-Butyl 2-(1-((benzyloxy)carbonyl)-3-hydroxyazetidin-3-yl)piperidine-1-carboxylate

Product 1

HCID 66769979tert-Butyl 2-(3-hydroxyazetidin-3-yl)piperidine-1-carboxylateYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl 2-(3-hydroxy-1-{[(phenylmethyl)oxy]carbonyl}azetidin-3-yl)piperidine-1-carboxylate (595 mg, 1.52 mmol), prepared using procedures similar to those described in Reference 5, in methanol (5 mL) was added catalytic palladium on carbon (5% wt). The heterogeneous mixture was stirred under a hydrogen gas atmosphere for 15 hours at ambient pressure and then was filtered. The filtrate was concentrated in vacuo to afford 385 mg, 1.50 mmol (98%) of 1,1-dimethylethyl 2-(3-hydroxyazetidin-3-yl)piperidine-1-carboxylate as a colorless film without further purification.

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-90b9ed63fd3a4e97bb7605e3d5f87a0e
Source dataset
uspto-grants-2011_03
Patent number
US07915250B2

Reaction notes

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