Tetrahydro-4H-pyran-4-one → (Tetrahydropyran-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine

HRID 1024386Notes

Reaction equation

HRID 1024386 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[O:3]1.[O:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[O:17]1[CH2:22][CH2:21][CH:20]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59497754(Tetrahydropyran-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amineYield 99.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (0.5 g, 2.28 mmol), tetrahydropyran-4-one (0.25 ml, 2.73 mmol) and sodium triacetoxy-borohydride (0.71 g, 3.42 mmol) in DCE (50 ml) was stirred at room temperature for 16 hours. The crude was filtered over diatomaceous earth, washed with DCM and the filtrate was evaporated in vacuo to yield D7 (0.69 g) that was used without further purification.

Workup

  1. filtrationThe crude was filtered over diatomaceous earth
  2. washwashed with DCM
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-1c95fa0f3b0841649051f4d69cb6dfb6
Source dataset
uspto-grants-2014_05
Patent number
US08722894B2

Reaction notes

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