Acetone → (1-Isopropylazetidin-3-yl)methanol hydrochloride

HRID 273076Notes

Reaction equation

HRID 273076 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([CH2:18][OH:19])[CH2:15]1)([C:8]1C=CC=CC=1)[C:2]1C=CC=CC=1.CC(C)=O.[ClH:24]>[OH-].[OH-].[Pd+2].CC(O)C>[ClH:24].[CH:1]([N:14]1[CH2:17][CH:16]([CH2:18][OH:19])[CH2:15]1)([CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 2758715(1-Benzhydrylazetidin-3-yl)methanol

Product 1

HCID 68575734(1-Isopropylazetidin-3-yl)methanol hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of (1-benzhydrylazetidin-3-yl)methanol (4.0 g, 15.8 mmol), acetone (20 ml), 2-propanol (80 ml), c.HCl (1.5 ml) and Pd(OH)2 was hydrogenated at 50 psi/50° for 18 hours. The reaction mixture was filtered through Arbocel® and concentrated in vacuo, the residue was triturated with diisopropyl ether (50 ml) to give the title compound as a pale green hygroscopic powder (2.6 g, 99%). LRMS ESI+m/z 130 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel®
  2. concentrationconcentrated in vacuo
  3. customthe residue was triturated with diisopropyl ether (50 ml)

Sources & evidence

ORD record
ord-28c3836971fa444982d09e540a765adb
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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