tert-Butyl 2-azido-6-azaspiro[3.4]octane-6-carboxylate → tert-Butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylate

HRID 336549Notes

Reaction equation

HRID 336549 reaction equation
[N:1]([CH:4]1[CH2:7][C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:5]1)=[N+]=[N-]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[NH2:1][CH:4]1[CH2:5][C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:7]1

Participants

3

Reactant 1

HCID 86660640tert-Butyl 2-azido-6-azaspiro[3.4]octane-6-carboxylate

Product 1

HCID 56962195tert-Butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylateYield 58.4%

Reagents, catalysts & solvents 1

HCID 131709914Lindlars catalystCatalyst

Procedure

The process is performed according to the procedure described in Example 6 (step 6.4). Starting with 1.33 g (5.30 mmol) of tert-butyl 2-azido-6-azaspiro[3.4]octane-6-carboxylate (isomer 2′) and 0.54 g (2.65 mmol) of Lindlar catalyst (PdCaCO3), 0.70 g of product is obtained in the form of an oil.

Sources & evidence

ORD record
ord-9b53e02da1154478abc6228db4266c52
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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