Pivalaldehyde → HCID 67334670, compound

HRID 1669860Notes

Reaction equation

HRID 1669860 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([CH:14]3[CH2:19][CH2:18][N:17]([C:20](=O)[C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:16][CH2:15]3)[N:11]([CH2:26][C:27]3[CH:40]=[CH:39][C:30]([C:31](NC4NN=NN=4)=[O:32])=[CH:29][CH:28]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CC(C)(C)[CH:43]=[O:44].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([CH:14]3[CH2:15][CH2:16][N:17]([CH2:20][C:21]([CH3:24])([CH3:22])[CH3:23])[CH2:18][CH2:19]3)[N:11]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([C:31]([O:44][CH3:43])=[O:32])=[CH:39][CH:40]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 12417PivalaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178447187HCID 178447187, compound

Product 1

HCID 67334670HCID 67334670, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate from Example 142 step F (100 mg, 0.225 mmol) in 1,2-dichloroethane (3 mL) was added trimethyl acetaldehyde (29 mg, 0.337 mmol) and sodium triacetoxy borohydride (71 mg, 0.337 mmol). After 16 hours the reaction was diluted with DCM (10 mL) and washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. This material was used in the next step without any further purification. LC-MS: 3.44 min; (M+H)=514.2.

Workup

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThis material was used in the next step without any further purification
  6. custom3.44 min

Sources & evidence

ORD record
ord-11c1f4d9a4a846989ecb8c863e219493
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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