tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → HCID 86727062, compound

HRID 1502012Notes

Reaction equation

HRID 1502012 reaction equation
[F:1][C:2]1[C:9]([CH:10]2[CH2:12][O:11]2)=[CH:8][CH:7]=[C:6]([F:13])[C:3]=1[C:4]#[N:5].[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]>C(O)C>[C:4]([C:3]1[C:2]([F:1])=[C:9]([CH:10]([OH:11])[CH2:12][N:24]2[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]2[CH2:27][OH:28])[CH:8]=[CH:7][C:6]=1[F:13])#[N:5]

Participants

4

Reactant 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 867270612,6-Difluoro-3-(oxiran-2-yl)benzonitrile

Product 1

HCID 86727062HCID 86727062, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

2,6-Difluoro-3-(oxiran-2-yl)benzonitrile (1.50 g, 8.28 mmol) and (S)-4-N—BOC-2-hydroxymethylpiperazine (2.40 g, 11.1 mmol) were suspended in ethanol (15 mL) then heated in a microwave apparatus for 30 min at 150° C. The reaction mixture was cooled and evaporated dryness. The residue was purified by chromatography through a 120 g Redi-sep column eluting with 5% MeOH/95% EtOAc to yield the title compound LC-MS: M+1=398.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated dryness
  3. customThe residue was purified by chromatography through a 120 g Redi-sep column
  4. washeluting with 5% MeOH/95% EtOAc

Sources & evidence

ORD record
ord-5cd549f554be4725a55a6b087e182886
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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