4-((Dimethylamino)methyl)phenol → tert-Butyl 3-(4-((dimethylamino)methyl)phenoxy)azetidine-1-carboxylate

HRID 1035202Notes

Reaction equation

HRID 1035202 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:3].CS(O[CH:17]1[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]1)(=O)=O>>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:17]2[CH2:18][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20]2)=[CH:9][CH:10]=1)[CH3:1]

Participants

3

Reactant 2

HCID 328954-((Dimethylamino)methyl)phenolHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Product 1

HCID 58043106tert-Butyl 3-(4-((dimethylamino)methyl)phenoxy)azetidine-1-carboxylateYield 87%

Procedure

Using a similar protocol as described in Example 29C employing 4-((dimethylamino)methyl)phenol (8.4 g, 55.5 mmol) and tert-butyl 3-(methylsulfonyloxy)azetidine-1-carboxylate (16.8 g, 66.7 mmol) as starting materials afforded 14.8 g (75%) of 33A as an oil. 1H NMR (500 MHz, CDCl3): δ 1.40 (s, 9H), 2.55 (s, 6H), 3.90 (s, 2H), 4.00 (m, 2H), 4.30 (m, 2H), 4.85 (m, 1H), 6.75 (d, 2H), 7.35 (d, 2H), MS (APCI+) m/z 307 [M+H]+.

Sources & evidence

ORD record
ord-0716665360224d64a029d34b3ba6faa7
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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