Sodium cyanoborohydride → Tert-butyl 2-(1-benzhydrylazetidin-3-yl)hydrazinecarboxylate

HRID 46357Notes

Reaction equation

HRID 46357 reaction equation
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:8]2[CH2:11][C:10](=[N:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[C:21]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 59436533Tert-butyl 2-(1-benzhydrylazetidin-3-ylidene)hydrazinecarboxylate

Product 1

HCID 59436626Tert-butyl 2-(1-benzhydrylazetidin-3-yl)hydrazinecarboxylateYield 94.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of tert-butyl 2-[1-(diphenylmethyl)azetidin-3-ylidene]hydrazinecarboxylate (Preparation 692, 15.8 g, 45 mmol) in acetic acid (126 ml) was added sodium cyanoborohydride (2.82 g, 45 mmol) portionwise at room temperature and stirred at room temperature for 4 hours. Then the reaction mixture was concentrated in vacuo. The pH was adjusted to 8-10 with 1M aqueous sodium hydroxide solution and extracted with dichloromethane (3×200 ml). The combined organic layer was washed with water (3×150 ml), saturated aqueous sodium chloride solution (150 ml), dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was triturated with diethyl ether to get 15 g (94%) of the title compound as a white solid.

Workup

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. extractionextracted with dichloromethane (3×200 ml)
  3. washThe combined organic layer was washed with water (3×150 ml), saturated aqueous sodium chloride solution (150 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was triturated with diethyl ether

Sources & evidence

ORD record
ord-cf9d27925e1e4dd1a899469b1eeec7e3
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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