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

HRID 1404352Notes

Reaction equation

HRID 1404352 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-41e7a9e0d1f14bf0a1044c608950db75
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

Loading…