tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → HCID 86727085, compound

HRID 2175871Notes

Reaction equation

HRID 2175871 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH:11]2[CH2:13][O:12]2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[OH:14][CH2:15][C@H:16]1[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1>CCO>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([CH:11]([OH:12])[CH2:13][N:21]2[CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:17][C@H:16]2[CH2:15][OH:14])=[CH:10][C:3]=1[O:2][CH3:1])#[N:6]

Participants

4

Reactant 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 552967592-Methoxy-4-(oxiran-2-yl)benzonitrile

Product 1

HCID 86727085HCID 86727085, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A Pyrex vessel was charged with magnetic stirring bar, (0.350 g, 2.00 mmol) of 2-methoxy-4-(oxiran-2-yl)benzonitrile, (0.457 g, 2.20 mmol) of tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate, and 6 mL of EtOH. Then it was introduced in the microwave reactor and irradiated at 150° C. for 3 hr. Then the mixture was cooled to room temperature and the solvent was evaporated and the resulting residue was purified by column chromatography (silica gel, 1-20% dichloromethane/MeOH) which afforded the title compound as a mixture of two diastereomers (1:1). LC/MS: (IE, m/z) [(M+1)-t-Bu]+=336.1.

Workup

  1. additionA Pyrex vessel was charged with magnetic stirring bar
  2. additionThen it was introduced in the microwave reactor
  3. customirradiated at 150° C. for 3 hr
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by column chromatography (silica gel, 1-20% dichloromethane/MeOH) which

Sources & evidence

ORD record
ord-f65ffdfb05884a2b8c474058eaa82b09
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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