tert-Butyl 4-formylpiperidine-1-carboxylate → HCID 178520740, compound

HRID 1486165Notes

Reaction equation

HRID 1486165 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][C:9]([NH:11][C@H:12]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([OH:24])=[O:23])[C:15]=3[O:14][B:13]2[OH:25])=[O:10])[CH2:4][CH2:3]1.[CH:26]([CH:28]1[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]1)=O>>[OH:25][B:13]1[C@@H:12]([NH:11][C:9](=[O:10])[CH2:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([NH:1][CH2:26][CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH2:3][CH2:4]2)[CH2:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([OH:24])=[O:23])[C:15]=2[O:14]1

Participants

3

Reactant 2

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 178511528HCID 178511528, compound

Product 1

HCID 178520740HCID 178520740, compound

Procedure

Prepared from (R)-3-(2-(trans-4-aminocyclohexyl)acetamido)-2-hydroxy-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid (Example 6) and tert-butyl 4-formylpiperidine-1-carboxylate following the procedure in Example 27. Boc group was removed by treatment with 4N HCl in dioxane. The product was purified using reverse phase HPLC to afford the titled compound. ESI-MS m/z 444 (MH)+.

Workup

  1. customBoc group was removed by treatment with 4N HCl in dioxane
  2. customThe product was purified

Sources & evidence

ORD record
ord-7e980252e5b44de6a99733bdd02ace80
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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