Methylhydrazine → (R)-tert-butyl 3-(2-methylhydrazinecarbonyl)piperidine-1-carboxylate

HRID 1465703Notes

Reaction equation

HRID 1465703 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][NH:18][NH2:19]>C(Cl)Cl>[CH3:17][NH:18][NH:19][C:14]([C@@H:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)=[O:16]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylate

Product 1

HCID 86695581(R)-tert-butyl 3-(2-methylhydrazinecarbonyl)piperidine-1-carboxylateYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Added a solution of N,N-dicyclohexylcarbodiimide (I M in CH2Cl2, 5 ml, 5 mmol) to a solution of (R)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (1 g, 4.36 mmol) and N-methyl hydrazine (0.3 g, 6.51 mmol) in CH2Cl2 (20 ml) then stirred for 1 hour. The precipitated solid was filtered, mother liquors were concentrated and residue purified by chromatography on silica gel eluting with 3% v/v MeOH/CH2Cl2 to yield (R)-tert-butyl 3-(2-methylhydrazinecarbonyl)piperidine-1-carboxylate as a white solid (0.85 g).

Workup

  1. filtrationThe precipitated solid was filtered
  2. concentrationmother liquors were concentrated
  3. customresidue purified by chromatography on silica gel eluting with 3% v/v MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a16f67a91c5340f3822918eeb2672492
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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