tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylate → tert-Butyl 4-[(3-ethoxycarbonylisoxazol-5-ylmethoxy-carbonylamino)methyl]-4-fluoropiperidine-1-carboxylate

HRID 1019697Notes

Reaction equation

HRID 1019697 reaction equation
[NH2:1][CH2:2][C:3]1([F:16])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[N+](C1C=CC([O:24][C:25]([O:27][CH2:28][C:29]2[O:33][N:32]=[C:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:30]=2)=O)=CC=1)([O-])=O>>[CH2:37]([O:36][C:34]([C:31]1[CH:30]=[C:29]([CH2:28][O:27][C:25]([NH:1][CH2:2][C:3]2([F:16])[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:7][CH2:8]2)=[O:24])[O:33][N:32]=1)=[O:35])[CH3:38]

Participants

3

Reactant 2

HCID 40152119tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylateHCID 66661006Ethyl 5-(4-nitrophenoxycarbonyloxymethyl)isoxazole-3-carboxylate

Product 1

HCID 66661123tert-Butyl 4-[(3-ethoxycarbonylisoxazol-5-ylmethoxy-carbonylamino)methyl]-4-fluoropiperidine-1-carboxylateYield 25.5%

Procedure

The process is performed according to the procedure described in Example 1 (step 1.6.). Starting with 0.70 g (3.01 mmol) of tert-butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylate (commercial) and 1.11 g (3.31 mmol) of ethyl 5-(4-nitrophenoxycarbonyloxymethyl)isoxazole-3-carboxylate, obtained in step 14.1., 0.33 g of pure product is obtained in the form of an orange-coloured oil.

Workup

  1. customobtained in step 14.1

Sources & evidence

ORD record
ord-90508ecd6652446db56b1ffcf62fc5e7
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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