Sodium Hydroxide → 1-Benzhydryl-3-methylazetidin-3-ol

HRID 237283

Reaction equation

HRID 237283 reaction equation
[CH:1]([N:14]1[CH2:17][C:16](=[O:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][Mg+].[Br-].[OH-].[Na+]>CCOCC>[CH:1]([N:14]1[CH2:17][C:16]([CH3:19])([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 178418689HCID 178418689, compound

Product 1

HCID 102439891-Benzhydryl-3-methylazetidin-3-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1-benzhydryl-azetidin-3-one (1.0 g, 4.2 mmol) in ether (100 mL) at 0° C. was added CH3MgBr (1.5 mL, 3M in ether). The mixture was warmed to rt over 1 h and 1N NaOH (3 mL) was added. The organic layer was concentrated providing the title compound (1.1 g). MS (ESI): mass calcd. for C17H19NO, 253.2; m/z found, 254.2 [M+H]+. 1H NMR (CDCl3): 7.42-7.11 (m, 10H), 4.32 (s, 1H), 3.14 (d, J=8.5 Hz, 2H), 2.96 (d, J=8.5 Hz, 2H), 1.43 (s, 3H).

Workup

  1. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-ba694aa1b8614138859310890ee21375
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Linked notes

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