Sodium Bicarbonate → HCID 67302850, compound

HRID 888763Notes

Reaction equation

HRID 888763 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[N:11][NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:8]2.C([BH3-])#N.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][NH:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:8]2

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 5003444Sodium cyanoborohydrideHCID 67303161HCID 67303161, compound

Product 1

HCID 67302850HCID 67302850, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, a solution of benzyl 2-(adamantan-2-ylidene)hydrazinecarboxylate (1.60 g, 5.40 mmol) in tetrahydrofuran (54 mL) was added with sodium cyanoborohydride (370 mg, 5.90 mmol) at room temperature, to which a solution of p-toluenesulfonic acid monohydrate (190 mg, 1.00 mmol) in tetrahydrofuran (10 mL) was dropped. The resultant was stirred at the same temperature for 5 hours. The reaction solution was added with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and benzyl 2-(adamantan-2-yl)hydrazinecarboxylate (1.54 g, 94.9%) was obtained as a white crystalline powder.

Workup

  1. additionwas dropped
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c2f992dc49444dc6844a175da37c7d53
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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