4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 58103852, compound

HRID 1627023Notes

Reaction equation

HRID 1627023 reaction equation
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][CH:7]1[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1([CH3:31])[C:21]([CH3:23])([CH3:22])[O:20][B:19]([C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[O:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][CH:7]1[CH2:12][CH2:11][CH:10]([NH:30][C:27]2[CH:26]=[CH:25][C:24]([B:19]3[O:20][C:21]([CH3:23])([CH3:22])[C:17]([CH3:31])([CH3:16])[O:18]3)=[CH:29][CH:28]=2)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 5049666Sodium triacetoxyborohydrideHCID 106094304-(tert-Butyldimethylsilyloxy)cyclohexanone

Product 1

HCID 58103852HCID 58103852, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexanone (1.72 ml, 6.85 mml) [C.A.S.55145-45-4], 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (1 g, 4.56 mmol) and sodium triacetoxy-borohydride (1.44 g, 6.85 mmol) in DCM (25 ml) was stirred at r.t. for 1 day. Then, the mixture was washed with NH4Cl (aqueous sat. solution). The organic layer was collected, dried (MgSO4) and evaporated in vacuo. The crude product thus obtained was purified by column chromatography (silica gel; heptane/EtOAc up to 5% as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate compound D32-a (trans) (0.566 g, 31%) and D32-b (cis) (1.089 g, 61%).

Workup

  1. washThen, the mixture was washed with NH4Cl (aqueous sat. solution)
  2. customThe organic layer was collected
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5ea110d198cf425cb1b6ed0ec264d8ec
Source dataset
uspto-grants-2014_07
Patent number
US08785486B2

Reaction notes

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