Azetidine → 1-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}azetidine

HRID 387357Notes

Reaction equation

HRID 387357 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.[CH3:5][C:6]1([CH3:20])[C:10]([CH3:12])([CH3:11])[O:9][B:8]([C:13]2[CH:14]=[C:15]([CH:18]=O)[S:16][CH:17]=2)[O:7]1.C([BH3-])#N.[Na+].[N-]=C=O>C1COCC1>[CH3:5][C:6]1([CH3:20])[C:10]([CH3:11])([CH3:12])[O:9][B:8]([C:13]2[CH:14]=[C:15]([CH2:18][N:1]3[CH2:4][CH2:3][CH2:2]3)[S:16][CH:17]=2)[O:7]1

Participants

6

Reactant 4

HCID 10422AzetidineHCID 105034IsocyanateHCID 5003444Sodium cyanoborohydride2×HCID 467397834-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde

Product 1

HCID 593327081-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}azetidineYield 59.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of azetidine (0.014 g, 0.252 mmol) in THF (1 mL) was added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbaldehyde (0.05 g, 0.210 mmol) in THF (1 mL) in 1-Dram vial and let stir for 30 minutes. Sodium Cyanoborohydride Resin (0.128 g, 0.583 mol, 2.33 mmol/g)) was then added to the mixture and let stir 3 days. The mixture was then agitated for 3 hrs with MP-Isocyanate Resin (0.135 g, 0.230 mmol, 1.7 mmol/g) and THF (2 mL). The reaction was resubjected to the same amounts of Sodium Cyanoborohydride Resin and amine as above and stirred for 2 days. The resins were then filtered and solvent concentrated to give 0.035 g of the title compound.

Workup

  1. stirringlet stir 3 days
  2. stirringstirred for 2 days
  3. filtrationThe resins were then filtered
  4. concentrationsolvent concentrated

Sources & evidence

ORD record
ord-9e59f8a168d241aabaa6158e5c3733b3
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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