Sodium Hydroxide → tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetate

HRID 2388653Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][OH:20])(=[O:12])=[O:11])=[C:5]([CH3:21])[CH:4]=1.[OH-].[Na+].[C:24]([O:28][C:29](=[O:32])[CH2:30]Br)([CH3:27])([CH3:26])[CH3:25]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:21])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][O:20][CH2:30][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:32])(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

n-Bu4NCl (7.52 g, 27.1 mmol) was added to a solution of (1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methanol (27.2 g, max. 73.8 mmol) in toluene/MC (150 ml/150 ml) and the mixture was cooled to 0° C. A 35% strength aqueous NaOH solution (300 ml) was then added. Bromoacetic acid tert-butyl ester (17.8 ml, 122 mmol) was then added dropwise to the reaction mixture and the mixture was stirred at room temperature for 3 hours. The organic phase was separated off, washed with water (3×300 ml), dried over Na2SO4 and concentrated in vacuo. Purification was carried out by chromatography on silica gel (heptane/ethyl acetate 3:1). The yield was 26.8 g (85% over 2 stages).

Workup

customThe organic phase was separated off
washwashed with water (3×300 ml)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customPurification

Sources & evidence

ORD record: ord-806c5ef24ffe4ef390e8f01ad5492103
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268814B2

Reaction notes

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