Sodium cyanoborohydride → Tert-butyl 4-(2-(tert-butoxycarbonyl)hydrazinyl)piperidine-1-carboxylate

HRID 1521819Notes

Reaction equation

HRID 1521819 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]=[C:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+]>O.C(O)(=O)C>[C:1]([O:5][C:6]([NH:8][NH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 20824233Tert-butyl 4-[(tert-butoxycarbonyl)hydrazono]piperidine-1-carboxylate

Product 1

HCID 20824232Tert-butyl 4-(2-(tert-butoxycarbonyl)hydrazinyl)piperidine-1-carboxylateYield 89.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To tert-butyl 4-[(tert-butoxycarbonyl)hydrazono]piperidine-1-carboxylate (15.7 g; 50.1 mmol; 1 eq.) in water (78.5 mL) and glacial acetic acid (78.5 mL) is added sodium cyanoborohydride (3.15 g; 50.1 mmol; 1 eq.) and the reaction mixture is stirred at rt overnight. The solvents are removed to near dryness and the product is extracted with AcOEt. The combined organic phase is washed with NaOH (1 M), dried over MgSO4, filtered and concentrated to afford: 14.1 g (89%) of the title compound. 1H NMR (300 MHz, DMSO): δ 8.22 (s, 1H), 4.61-4.14 (m, 1H), 3.81-3.55 (m, 2H), 3.08-2.67 (m, 2H), 1.73-1.50 (m, 2H), 1.38 (s, 18H), 1.22-0.98 (m, 2H).

Workup

  1. customThe solvents are removed
  2. extractionthe product is extracted with AcOEt
  3. washThe combined organic phase is washed with NaOH (1 M)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford

Sources & evidence

ORD record
ord-cecf422f8e2b43468d9352db9d5a0f6e
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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