Sodium Carbonate → {1-[1-(Diphenylmethyl)azetidin-3-yl]-4-(phenylcarbonyl)piperazin-2-yl}methanol

HRID 2362085Notes

Reaction equation

[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH:13]3[CH2:18][OH:19])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]([O-:29])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:20]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH:10]([N:12]3[CH2:17][CH2:16][N:15]([C:26]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[O:29])[CH2:14][CH:13]3[CH2:18][OH:19])[CH2:11]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 37c (1.03 mmol) was dissolved in CH2Cl2 (5 mL) and cooled in an ice water bath to 0° C. A 10% aqueous Na2CO3 solution (5 mL) was added and a solution of compound 37d (143 μL, 1.23 mmol) dissolved in CH2Cl2 (1 mL) was added dropwise. The resultant mixture was allowed to warm to 20° C. and then stirred rapidly for 62 h. CH2Cl2 (10 mL) was added to the reaction mixture and the aqueous phase was extracted with CH2Cl2 (2×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to give compound 37e (465 mg) as an off white foam. Compound 37e was used in the following step without further purification. 1H NMR (400 MHz, CDCl3): δ 7.39 (m, 9H), 7.22-7.32 (m, 4H), 7.14-7.23 (m, 2H), 4.35 (s, 1H), 4.07 (br. s, 1H), 3.30-3.71 (complex, 8H), 2.2-3.0 (complex, 6H); LCMS m/z (M+H+) 442.2.

Workup

additionwas added dropwise
temperatureto warm to 20° C.
extractionthe aqueous phase was extracted with CH2Cl2 (2×20 mL)
washThe combined organic extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-dc8cf62644ec4a198798e453a44723c9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691805B2

Reaction notes

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