Hydrochloric Acid → tert-butyl-4-[(1R)-1-aminoethyl]benzoate hydrochloride

HRID 1049081Notes

Reaction equation

HRID 1049081 reaction equation
C([S@@]([NH:7][C@@H:8]([C:10]1[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:12][CH:11]=1)[CH3:9])=O)(C)(C)C.[ClH:23]>CO>[ClH:23].[C:17]([O:16][C:14](=[O:15])[C:13]1[CH:12]=[CH:11][C:10]([C@H:8]([NH2:7])[CH3:9])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58417313tert-butyl 4-[(1R)-1-{[(S)-tert-butylsulfinyl]amino}ethyl]benzoate

Product 1

HCID 67395949tert-butyl-4-[(1R)-1-aminoethyl]benzoate hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a microwave vial containing tert-butyl 4-[(1R)-1-{[(S)-tert-butylsulfinyl]amino}ethyl]benzoate (0.052 g, 0.16 mmol) was added hydrochloric acid (0.08 mL, 0.32 mmol, 4.0 M of in 1,4-dioxane), and methanol (2 mL). This mixture was stirred at rt for 2 h, and then evaporated to dryness to afford tert-butyl-4-[(1R)-1-aminoethyl]benzoate hydrochloride as a white solid. LC-MS: (FA) ES+ 222.

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-e2a9b72e9f92426ca7d15a61a680dfca
Source dataset
uspto-grants-2016_07
Patent number
US09382197B2

Reaction notes

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