146721-06-4

Basic information

• Product Name: (+/-)-1-(1,3-Benzodioxol-5-yl)-2-broMo-1-pentanone
• Synonyms: 1-Pentanone, 1-(1,3-benzodioxol-5-yl)-2-broMo-;(+/-)-1-(1,3-Benzodioxol-5-yl)-2-broMo-1-pentanone
• CAS NO: 146721-06-4
• Molecular Formula: C₁₂H₁₃BrO₃
• Molecular Weight: 285
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 146721-06-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 369.7±42.0 °C(Predicted)
• Appearance: /
• Density: 1.460±0.06 g/cm3(Predicted)
• Solubility: Chloroform,
• CAS DataBase Reference: (+/-)-1-(1,3-Benzodioxol-5-yl)-2-broMo-1-pentanone(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-1-(1,3-Benzodioxol-5-yl)-2-broMo-1-pentanone(146721-06-4)
• EPA Substance Registry System: (+/-)-1-(1,3-Benzodioxol-5-yl)-2-broMo-1-pentanone(146721-06-4)

Safety Data

• Hazardous Substances Data: 146721-06-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Intermediate in the preparation of Sesquilignan analogs.

Synthetic route

1-(benzo[d]-1,3-dioxol-5-yl)pentan-1-one (63740-98-7) → (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4)

Conditions	Yield
With bromine; acetic acid at 20℃; for 2h;	89%
With bromine; acetic acid at 20℃; for 3h;	87%
With aluminum (III) chloride; bromine In diethyl ether at 0 - 20℃; for 0.25h; Inert atmosphere;	86%
With bromine In chloroform at 20℃;
With bromine; acetic acid In dichloromethane

(+/-)-(1R*,2R*/S*)-2-bromo-1-hydroxy-1-(3,4-methylenedioxyphenyl)pentane → (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4)

Conditions	Yield
With jones reagent In acetone at 0℃; for 0.25h;	82%

piperonal (120-57-0) + alkali → (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) NaH / 1) DMSO, r.t., 15 min, 2) THF, r.t., 2 h 2: 98 percent / N-bromosuccinimide, H2O / dimethylsulfoxide / 0.25 h / Ambient temperature 3: 82 percent / Jones reagent / acetone / 0.25 h / 0 °C View Scheme

(Z)-1-(3,4-methylenedioxyphenyl)-1-pentene (81392-98-5) → (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / N-bromosuccinimide, H2O / dimethylsulfoxide / 0.25 h / Ambient temperature 2: 82 percent / Jones reagent / acetone / 0.25 h / 0 °C View Scheme

piperonal (120-57-0) → (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0.5 h / 5 - 20 °C / Inert atmosphere 2: manganese(IV) oxide / chloroform; tetrahydrofuran / 1 h / Reflux 3: bromine / chloroform / 20 °C View Scheme

1-(benzo[d][1,3]dioxol-5-yl)pentan-1-ol (5422-01-5) → (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: manganese(IV) oxide / chloroform; tetrahydrofuran / 1 h / Reflux 2: bromine / chloroform / 20 °C View Scheme

piperonylonitrile (4421-09-4) → (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium / diethyl ether / 3 h / Inert atmosphere; Reflux 1.2: 4 h / Reflux 2.1: acetic acid; bromine / 3 h / 20 °C View Scheme

Methylenedioxybenzene (274-09-9) → (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: tin(IV) chloride / dichloromethane / 3 - 10 °C 2: bromine; acetic acid / dichloromethane View Scheme

n-valeryl chloride (638-29-9) → (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: tin(IV) chloride / dichloromethane / 3 - 10 °C 2: bromine; acetic acid / dichloromethane View Scheme

pyrrolidin-3-ol (40499-83-0) + (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → 1-(benzo[D][1,3]dioxol-5-yl)-2-(3-hydroxypyrrolidin-1-yl)-1-pentanone

Conditions	Yield
With potassium carbonate In tetrahydrofuran Inert atmosphere;	65%

(3R)-pyrrolidinol (40499-83-0, 83220-72-8, 100243-39-8, 2799-21-5) + (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (RS)-1-(benzo[d][1,3]dioxol-5-yl)-2-((R)-3-hydroxypyrrolidin-1-yl)pentanone

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; Inert atmosphere;	60%

3-benzyloxy-4-hydroxybenzaldehyde (50773-56-3) + (+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-3-Benzyloxy-4-<(1R*)-1-(3,4-methylenedioxybenzoyl)butoxy>benzaldehyde (146721-08-6)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h; Yield given. Multistep reaction;

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(2R*,3R*/S*)-2-Propyl-6-hydroxy-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxane

Conditions	Yield
Multi-step reaction with 5 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(2R*,3R*/S*)-2-Propyl-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-6-carbaldehyde

Conditions	Yield
Multi-step reaction with 4 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(2R*,3R*/S*)-2-Propyl-6-methoxy-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxane

Conditions

Yield

Multi-step reaction with 6 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(2R*)-3-Benzyloxy-4-<(1R*)-1-hydroxy-1-(3,4-methylenedioxyphenyl)-2-pentyloxy>benzaldehyde

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (2S,3S)-2-Benzo[1,3]dioxol-5-yl-6-dimethoxymethyl-7-methoxy-3-propyl-2,3-dihydro-benzo[1,4]dioxine

Conditions

Yield

Multi-step reaction with 7 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → 1-Benzo[1,3]dioxol-5-yl-2-(2-benzyloxy-4-dimethoxymethyl-phenoxy)-pentan-1-one

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(1S*,5R*,6S*)-6-<(2''R*,3''R*)/(2''S*,3''S*)-2''-Propyl-6-methoxy-3''-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl>-1'-hydroxy-3,7-dioxabicyclo<3.3.0>octan-2-one

Conditions

Yield

Multi-step reaction with 14 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h 8: 96 percent / 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature 9: 1) lithium diisopropylamide 10: 97 percent 11: 56 percent / LiAlH4 13: 1) mesylation, 2) desulfonation View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(3S*,4R*)-3-<(1'R*/S*)-1-<(2''R*,3''R*)/(2''S*,3''S*)-2''-Propyl-6-methoxy-3''-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl>-1'-hydroxymethyl>-4-vinyldihydro-2(3H)-furanone

Conditions

Yield

Multi-step reaction with 9 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h 8: 96 percent / 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature 9: 1) lithium diisopropylamide View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(3S*,4R*)-3-<(1'R*/S*)-1-<(2''R*,3''R*)/(2''S*,3''S*)-2''-Propyl-6-methoxy-3''-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl>-1'-<(tert-butyldimethylsilyl)oxy>methyl>-4-vinyldihydro-2(3H)-furanone

Conditions

Yield

Multi-step reaction with 10 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h 8: 96 percent / 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature 9: 1) lithium diisopropylamide 10: 97 percent View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(4R*)-4-<(1'R*/S*)-1-<(2''R*,3''R*)/(2''S*,3''S*)-2''-Propyl-6-methoxy-3''-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl>-1'-<(tert-butyldimethylsilyl)oxy>methyl>-3-methylenedihydro-2(3H)-furanone

Conditions

Yield

Multi-step reaction with 13 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h 8: 96 percent / 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature 9: 1) lithium diisopropylamide 10: 97 percent 11: 56 percent / LiAlH4 13: 1) mesylation, 2) desulfonation View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(2R*,3R*)-2-<(1'R*/S*)-1-<(2''R*,3''R*)/(2''S*,3''S*)-2''-Propyl-6-methoxy-3''-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl>-1'-<(tert-butyldimethylsilyl)oxy>methyl>-3-vinyl-1,4-butanediol

Conditions

Yield

Multi-step reaction with 11 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h 8: 96 percent / 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature 9: 1) lithium diisopropylamide 10: 97 percent 11: 56 percent / LiAlH4 View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(3R*,4R*)-4-<(1'R*/S*)-1-<(2''R*,3''R*)/(2''S*,3''S*)-2''-Propyl-6-methoxy-3''-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl>-1'-<(tert-butyldimethylsilyl)oxy>methyl>-3-hydroxymethyldihydro-2(3H)-furanone

Conditions

Yield

Multi-step reaction with 12 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h 8: 96 percent / 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature 9: 1) lithium diisopropylamide 10: 97 percent 11: 56 percent / LiAlH4 View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(1S*,2R*,5R*,6S*)-6-<(2''R*,3''R*)/(2''S,3''S)-2''-Propyl-6''-methoxy-3''-(3,4-methylenedioxyphenyl)-1'',4''-benzodioxan-7''-yl>-2-(2',6'-dimethoxyphenoxy)-1-hydroxy-3,7-dioxabicyclo<3.3.0>octane

Conditions

Yield

Multi-step reaction with 15 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h 8: 96 percent / 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature 9: 1) lithium diisopropylamide 10: 97 percent 11: 56 percent / LiAlH4 13: 1) mesylation, 2) desulfonation 15: 1) DIBALH View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(2R*,3R*)-2-Propyl-6-methoxy-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-carbaldehyde

Conditions

Yield

Multi-step reaction with 8 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h 8: 96 percent / 2 N HCl / tetrahydrofuran / 1 h / Ambient temperature View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → (+/-)-(2R*,3S*)-2-Propyl-6-methoxy-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-carbaldehyde

Conditions

Yield

Multi-step reaction with 7 steps 1: 1) K2CO3, 18-crown-6 / 1) CH3CN, r.t., 1 h, 2) CH3CN, r.t., 18 h 2: NH4Cl / methanol; tetrahydrofuran / 2 h / Heating 3: 1) NaBH4, 2) 2 N HCl / 1) EtOH, THF, r.t., 1 h, 2) r.t., 30 min 4: 94 percent / sulfuric acid, acetic acid / 0.17 h / 70 - 80 °C 5: 1) m-chloroperbenzoic acid, KF, 2) 1 N NaOH / 1) CH2Cl2, r.t., 16 h, 2) EtOH, r.t., 1 h 6: 1) NaH / 1) DMF, r.t., 2 h, 2) r.t., 1 h 7: 1) POCl3 / 1) r.t., 2) DMF View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → C20H25NO7

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 20 °C / Inert atmosphere 2: pyridine / 20 °C View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → 2-amino-1-(benzo[d]-1,3-dioxol-5-yl)pentan-1-one (1477611-87-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide / methanol / 12 h / 20 °C 2: tin(II) chloride dihdyrate / ethanol / 2 h / 0 - 20 °C View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → 2-amino-1-(benzo[d]-1,3-dioxol-5-yl)pentan-1-one hydrochloride (1477462-91-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium azide / methanol / 12 h / 20 °C 2: tin(II) chloride dihdyrate / ethanol / 2 h / 0 - 20 °C 3: hydrogenchloride / water View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → C12H13N3O3 (1477611-88-3)

Conditions	Yield
With sodium azide In methanol at 20℃; for 12h;

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → S-(-)-MDPV*(+)-BTA

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 0 - 20 °C 2: acetone; diethyl ether View Scheme

(+/-)-(1R*)-1-Bromo-1-(3,4-methylenedioxybenzoyl)butane (146721-06-4) → R-(+)-MDPV*(-)-BTA

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether / 0 - 20 °C 2: acetone; diethyl ether 3: sodium carbonate / water View Scheme

Upstream product

• 120-57-0 piperonal 
• 81392-98-5 (Z)-1-(3,4-methylenedioxyphenyl)-1-pentene 
• 63740-98-7 1-(benzo[d]-1,3-dioxol-5-yl)pentan-1-one 
• 5422-01-5 1-(benzo[d][1,3]dioxol-5-yl)pentan-1-ol 
• 4421-09-4 piperonylonitrile 
• 274-09-9 Methylenedioxybenzene 
• 638-29-9 n-valeryl chloride 

Downstream Products

• 687603-66-3 MDPV 
• 24622-62-6 (R/S)-1-((benzo[d][1,3]dioxol-5-yl)-2-(pyrrolidin-1-yl)pentan-1-one) hydrochloride 

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The invention provides a methylenedioxypyrovalerone artificial antigen preparation method, which comprises: preparing hapten, wherein a bromobutane Grignard reagent is prepared in anhydrous diethyl ether by using bromobutane and a metal magnesium as raw materials, methylenedioxypyrovalerone with hydroxyl linked on a pyrrole ring is prepared by using the bromobutane Grignard reagent and 3,4-methylenedioxybenzonitrile as raw materials through carbonylation, bromination and pyrrole alcohol amination, and finally hapten containing long arm carboxyl is prepared by carrying out a reaction on succinic anhydride and the hydroxyl on the pyrrole ring; and coupling the hapten and protein to synthesize artificial antigen, wherein the hapten and bovine serum albumin are coupled through a carbodiimide-catalyzed active ester process to prepare the methylenedioxypyrovalerone artificial antigen. According to the present invention, the prepared methylenedioxypyrovalerone artificial antigen can be used for immunizing animals to obtain corresponding antibodies so as to be used for the researches on various methylenedioxypyrovalerone immunoassay and be used as the key raw material for the production ofmethylenedioxypyrovalerone immunochromatographic kits.

Immunoassay for pyrrolidinophenones

The invention describes antibodies that bind molecules of the pyrrolidinophenone class of synthetic drugs. The antibodies are derived from novel chemical intermediates, haptens and immunogens and are used in methods and kits to detect and quantify pyrrolidinophenones.