Hydrochloric Acid → (S)-benzyl 3-(hydroxymethyl)piperazine-1-carboxylate hydrochloride

HRID 2063314Notes

Reaction equation

HRID 2063314 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:6][CH2:5][N:4]1C(OC(C)(C)C)=O.[ClH:26]>C(#N)C>[ClH:26].[OH:1][CH2:2][C@H:3]1[NH:4][CH2:5][CH2:6][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69745232(S)-4-benzyl 1-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate

Product 1

HCID 16124474(S)-benzyl 3-(hydroxymethyl)piperazine-1-carboxylate hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Benzyl 1-tert-butyl (2S)-2-(hydroxymethyl)piperazine-1,4-dicarboxylate (see WO 02/000631; 1.6 g, 4.6 mmol was dissolved in acetonitrile (25 mL) and to the resultant solution was added concentrated HCl (1 mL). The mixture was stirred at RT overnight and then the solvent was removed by evaporation. There was obtained 1.3 g (100%) of benzyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate hydrochloride as a colorless oil. 1H NMR (500 MHz, CD3OD): 3.1-3.4 (m, 5H), 3.7 (m, 1H), 3.8 (m, 1H), 4.2 (m, 2H), 5.2 (m, 2H), 7.2-7.4 (m, 5H); LCMS: m/z 251 (M+1)+.

Workup

  1. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-8ec03afe6d364dc6a19e45592405f8df
Source dataset
uspto-grants-2012_10
Patent number
US08288370B2

Reaction notes

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