Benzhydrylamine → HCID 58687990, compound

HRID 132851Notes

Reaction equation

HRID 132851 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:13]=[C:12]([O:20][CH3:21])[C:11]=1[CH2:22][CH:23]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:25][CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:26]([NH:25][CH2:23][CH2:22][C:11]1[C:12]([O:20][CH3:21])=[N:13][C:14]([C:16]([F:17])([F:18])[F:19])=[CH:15][C:10]=1[CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2])([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58687952HCID 58687952, compound

Product 1

HCID 58687990HCID 58687990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the compound from Step H above (1.55 g, 4.26 mmol), aminodiphenylmethane (1.11 mL, 6.40 mmol), and powdered 4 Å molecular sieves (2.80 g) in dichloromethane (20 mL) was stirred for 30 min. Then sodium triacetoxyborohydride (132 mg, 0.625 mmol) was added. The resultant mixture was stirred overnight, diluted with dichloromethane, filtered, and the filtrate was washed with saturated aqueous sodium carbonate solution. The layers were separated, and the aqueous solution was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure, and the residue was purified by flash chromatography (silica gel; dichloromethane as eluant) to yield the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.48 (s, 1H), 7.18-7.38 (m, 10H), 4.84 (s, 1H), 4.78 (s, 2H), 3.81 (s, 3H), 2.77 (m, 4H), 1.62 (br s, 1H), 0.97 (s, 9H), 0.12 (s, 6H). LC/MS: 531 (M+1).

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed with saturated aqueous sodium carbonate solution
  3. customThe layers were separated
  4. extractionthe aqueous solution was extracted with dichloromethane
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by flash chromatography (silica gel; dichloromethane as eluant)

Sources & evidence

ORD record
ord-b90ba2aee04d4f84b29fe443d96ba551
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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