Hydrochloric Acid → (3R,4R,7R)-4-Amino-7-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol

HRID 229842Notes

Reaction equation

HRID 229842 reaction equation
Cl.C(OC(=O)[NH:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]([CH3:16])[N:12]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)(=[O:19])=[O:18])[CH2:11][C@H:10]1[OH:26])(C)(C)C>O1CCOCC1.CO.C1(C)C=CC=CC=1>[NH2:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]([CH3:16])[N:12]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)(=[O:19])=[O:18])[CH2:11][C@H:10]1[OH:26]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 69000299[(3R,4R,7R)-3-Hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 58665043(3R,4R,7R)-4-Amino-7-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

HCl in dioxane (4.0 M, 10 ml) was added to a stirred solution. [(3R,4R,7R)-3-Hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-yl]-carbamic acid tert-butyl ester (0.6 g, 1.55 mmol) in MeOH (10 ml). The reaction mixture was stirred for 1 h at RT, then was diluted with toluene (20 ml), concentrated in vacuo by rotary evaporation and was used in the next reaction without further purification (0.5 g, quantitative): Electrospray mass spec: M+H+=286.2.

Workup

  1. concentrationconcentrated in vacuo by rotary evaporation
  2. customwas used in the next reaction without further purification (0.5 g, quantitative)

Sources & evidence

ORD record
ord-1acf8021704c456695a7bae3f4adc53f
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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