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Benzophenone imine → tert-Butyl 3-(6-(Diphenylmethyleneamino)pyridin-3-yl)azetidine-1-carboxylate

HRID 1772128
Notes
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Reaction equation

HRID 1772128 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.[C:19](=[NH:32])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:20]1([C:19](=[N:32][C:2]2[N:7]=[CH:6][C:5]([CH:8]3[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]3)=[CH:4][CH:3]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 57537370Tert-butyl 3-(6-chloropyridin-3-yl)azetidine-1-carboxylate

Product 1

HCID 86697066tert-Butyl 3-(6-(Diphenylmethyleneamino)pyridin-3-yl)azetidine-1-carboxylateYield 79.1%

Reagents, catalysts & solvents

1
HCID 76545419Dibenzylideneacetone dipalladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A 500-mL round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 117a (2.00 g, 7.46 mmol), benzophenoneimine (1.62 g, 8.96 mmol), sodium tert-butoxide (1.00 g, 10.4 mmol), (dibenzylideneacetone)-dipalladium(0) (340 mg, 0.373 mmol) and rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (700 mg, 1.12 mmol), and the reaction was heated at 100° C. for 3 h. After this time the reaction was cooled to room temperature and concentrated under reduced pressure. The resulting oil was purified by column chromatography to afford a 79% yield (2.44 g) of 117b as a brown solid: mp 104-105° C.; 1H NMR (500 MHz, CDCl3) δ 8.20 (d, 1H, J=2.0 Hz), 7.85 (br s, 2H), 7.52 (br s, 1H), 7.44 (br s, 2H), 7.47 (dd, 1H, J=8.5, 2.0 Hz), 7.17 (br s, 5H), 6.61 (d, 1H, J=8.5 Hz), 4.30 (t, 2H, J=8.5 Hz), 3.86 (dd, 2H, J=8.5, 4.5 Hz), 3.62 (m, 1H), 1.45 (s, 9H); MS (ESI+) m/z 413.8 (M+H).

Workup

  1. customA 500-mL round-bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureAfter this time the reaction was cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-2b2bccff976849edb0ea5e3553233529
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249123B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes