Azepane → 1-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}hexahydro-1H-azepine

HRID 656120Notes

Reaction equation

HRID 656120 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][C:9]1([CH3:23])[C:13]([CH3:15])([CH3:14])[O:12][B:11]([C:16]2[CH:17]=[C:18]([CH:21]=O)[S:19][CH:20]=2)[O:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N-]=C=O>C1COCC1>[CH3:8][C:9]1([CH3:23])[C:13]([CH3:14])([CH3:15])[O:12][B:11]([C:16]2[CH:17]=[C:18]([CH2:21][N:1]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[S:19][CH:20]=2)[O:10]1

Participants

6

Reactant 4

HCID 8119AzepaneHCID 105034IsocyanateHCID 5049666Sodium triacetoxyborohydrideHCID 467397834-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde

Product 1

HCID 593327881-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}hexahydro-1H-azepineYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of hexahydro-1H-azepine (0.025 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 triacetoxyborohydride (0.225 g, 0.582 mmol) was then added to the mixture and let stir 18 h. The mixture was then agitated for 1 hour with MP-Isocyanate Resin (0.135 g, 0.230 mmol, 1.7 mmol/g) and THF (2 mL). The solution was filtered and the resin was washed with THF (4 mL×2). The combined solution was concentrated, giving 0.055 g (82%) of the title compound.

Workup

  1. stirringlet stir 18 h
  2. filtrationThe solution was filtered
  3. washthe resin was washed with THF (4 mL×2)
  4. concentrationThe combined solution was concentrated

Sources & evidence

ORD record
ord-b20ee6b6459d4e789cd6d10d2b825635
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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