Hydrochloric Acid → HCID 67334527, compound

HRID 1670631Notes

Reaction equation

HRID 1670631 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][C@@H:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[N+:23]([O-:25])=[O:24])[C@H:11]([OH:26])[CH2:10]1)=O)(C)(C)C>O1CCOCC1.ClCCl>[ClH:1].[Br:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C@@H:12]2[CH2:13][CH2:14][NH:9][CH2:10][C@H:11]2[OH:26])=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67335873(3R,4R)-4-(4-Bromo-2-nitro-phenylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67334527HCID 67334527, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4.0 M hydrogen chloride in dioxane (70 mL) slowly to a solution of (3R,4R)-4-(4-bromo-2-nitro-phenylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.027 mol, 11.5 g) in dry dichloromethane (40 mL) at room temperature and stir for 16 h. Filter the precipitate and dry under vacuum to obtain the title compound (8.68 g, 89%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 1.81-1.86 (m, 1H), 2.39-2.44 (m, 1H), 3.02-3.07 (m, 1H), 3.18-3.26 (m, 1H), 3.34-3.40 (m, 1H), 3.45 (dd, 1H), 3.87-3.91 (m, 2H), 7.17 (d, 1H), 7.61 (dd, 1H), 8.28 (d, 1H).

Workup

  1. filtrationFilter the precipitate
  2. customdry under vacuum

Sources & evidence

ORD record
ord-eba2ef889b814b6ba150b250fe7fceb5
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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