tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → HCID 86727077, compound

HRID 1502029Notes

Reaction equation

HRID 1502029 reaction equation
[CH3:1][C:2]1[C:6]([CH:7]2[CH2:9][O:8]2)=[CH:5][S:4][C:3]=1[C:10]#[N:11].[OH:12][CH2:13][C@H:14]1[NH:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1>CCO>[C:10]([C:3]1[S:4][CH:5]=[C:6]([CH:7]([OH:8])[CH2:9][N:19]2[CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:15][C@H:14]2[CH2:13][OH:12])[C:2]=1[CH3:1])#[N:11]

Participants

4

Reactant 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 86727076HCID 86727076, compound

Product 1

HCID 86727077HCID 86727077, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-methyl-4-(oxiran-2-yl)thiophene-2-carbonitrile (1.3 g, 7.9 mmol) and tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate (2.0 g, 9.5 mmol) in 5 mL of EtOH was heated in a microwave apparatus at 140° C. for 90 minutes and then cooled down. The reaction mixture was concentrated, and the residue was purified by column chromatography (DCM: MeOH=10:1) to afford the title compound.

Workup

  1. temperaturecooled down
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by column chromatography (DCM: MeOH=10:1)

Sources & evidence

ORD record
ord-7d0d3079ac0b4e738d0d9e3eb938c12f
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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