Dimethylamine → HCID 68955565, compound

HRID 2378053Notes

Reaction equation

HRID 2378053 reaction equation
[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3([CH:27]=O)[CH2:26][CH2:25]3)[O:15][N:14]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:31][NH:32][CH3:33].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O1CCCC1>[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3([CH2:27][N:32]([CH3:33])[CH3:31])[CH2:26][CH2:25]3)[O:15][N:14]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86613308HCID 86613308, compound

Product 1

HCID 68955565HCID 68955565, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture consisting of 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropanecarbaldehyde (Examples 14-17 General Procedure, Step A, 0.51 g) in dichloromethane (20 mL) is added sequentially a solution consisting of dimethylamine in tetrahydrofuran (2.0 M, 2 mL) followed by sodium triacetoxyborohydride (0.75 g.) The mixture is agitated overnight at room temperature under a nitrogen atmosphere. The mixture is diluted with dichloromethane (20 mL) and is washed twice with brine solution. The organic layer is separated, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography to afford the synthetic intermediate (1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropylmethyl)-dimethyl-amine (0.251 g)

Workup

  1. additionis added sequentially a solution
  2. washis washed twice with brine solution
  3. customThe organic layer is separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrate is purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-e92fe6d4fbff4499ad1028bb5f7ec746
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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