tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → HCID 117690307, compound

HRID 1502089Notes

Reaction equation

HRID 1502089 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:11]1[CH2:13][O:12]1.[C:14]([N:21]1[CH2:26][CH2:25][NH:24][C@H:23]([CH2:27][OH:28])[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>CCO>[OH:12][CH:11]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH3:1])[CH2:13][N:24]1[CH2:25][CH2:26][N:21]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:22][C@H:23]1[CH2:27][OH:28]

Participants

4

Reactant 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 89618828HCID 89618828, compound

Product 1

HCID 117690307HCID 117690307, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Methyl-3-nitrophenyl)oxirane (1.47 g, 8.20 mmol) was dissolved in EtOH (10 mL) then added (S)-4N—BOC-2-hydroxymethyl-piperazine (3.19 g, 14.77 mmol) and microwaved at 140° C. for 1 hr. Solvent was evaporated and the residue was purified by chromatography through a 120 g ISCO Redi-Sep column eluting with 0-20% ethyl acetate:hexane to yield the title compound: LC-MS (IE, m/z): 396 [M+1];

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by chromatography through a 120 g ISCO Redi-Sep column
  3. washeluting with 0-20% ethyl acetate

Sources & evidence

ORD record
ord-04bc4dc567a34af08b6e0b475cca3b01
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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