Benzylamine → HCID 86628107, compound

HRID 2245242Notes

Reaction equation

HRID 2245242 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C@@H:13]([C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[CH3:14])[C@@H:8]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C@@H:7]1[CH:36]=O)(=[O:3])[CH3:2].[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:1]([O:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C@@H:13]([C:15]2[CH:16]=[C:17]([C:25]([F:26])([F:28])[F:27])[CH:18]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:20]=2)[CH3:14])[C@@H:8]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C@@H:7]1[CH2:36][NH:45][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86628108HCID 86628108, compound

Product 1

HCID 86628107HCID 86628107, compoundYield 97.5%

Procedure

A mixture of aldehyde (0.56 g, 1.0 mmol) from Step L, benzylamine (0.15 mL, 1.4 mmol) and sodium triacetoxy borohydride (1.0 g, 4.7 mmol) in 50 mL dimethyl chloride was stirred at room temperature for 12 hr. The mixture was washed with sat. aq. NaHCO3, then brine, dried over MgSO4 and filtered. The solvent was evaporated under vacuum to give an oil (0.61 g), which was used in the next step without purification. MS: (MH)+ 624.5.

Workup

  1. washThe mixture was washed with sat. aq. NaHCO3
  2. dry with materialbrine, dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-60e7421796904ddaaae3386352245993
Source dataset
uspto-grants-2010_03
Patent number
US07683068B2

Reaction notes

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