Hydrochloric Acid → (S)-3-amino-1-(2-hydroxyethyl)azepan-2-one hydrochloride

HRID 912461Notes

Reaction equation

HRID 912461 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]([NH:18]C(=O)OC(C)(C)C)[C:12]1=[O:26])(C(C)(C)C)(C)C.[ClH:27].O1CCOCC1>ClCCl>[ClH:27].[NH2:18][C@H:13]1[CH2:14][CH2:15][CH2:16][CH2:17][N:11]([CH2:10][CH2:9][OH:8])[C:12]1=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57736566(S)-tert-butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxoazepan-3-ylcarbamate

Product 1

HCID 67417248(S)-3-amino-1-(2-hydroxyethyl)azepan-2-one hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxoazepan-3-ylcarbamate (prepared according to Example 15; 243 mg, 0.629 mmol) in dichloromethane (2 mL) was added 4M hydrogen chloride in dioxane (2 mL, 8 mmol), and the reaction mixture was allowed to stir at ambient temperature for 16 hours. The reaction mixture was concentrated to yield (S)-3-amino-1-(2-hydroxyethyl)azepan-2-one hydrochloride (131 mg, 100%), which was taken on to the next reaction without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-6dd5bfefbdcb4809a76bc79af12814b9
Source dataset
uspto-grants-2011_09
Patent number
US08026233B2

Reaction notes

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