tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → HCID 117690300, compound

HRID 1502041Notes

Reaction equation

HRID 1502041 reaction equation
[CH3:1][C:2]1[C:3]([CH:12]2[CH2:14][O:13]2)=[CH:4][C:5]2[CH2:9][O:8][C:7](=[O:10])[C:6]=2[CH:11]=1.[OH:15][CH2:16][C@H:17]1[NH:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1>CCO>[OH:15][CH2:16][C@H:17]1[N:22]([CH2:14][CH:12]([OH:13])[C:3]2[C:2]([CH3:1])=[CH:11][C:6]3[C:7](=[O:10])[O:8][CH2:9][C:5]=3[CH:4]=2)[CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1

Participants

4

Reactant 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 595686626-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one

Product 1

HCID 117690300HCID 117690300, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-methyl-5-(oxiran-2-yl)-2-benzofuran-1(3H)-one (750 mg, 3.95 mmol) and tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate (1.02 g, 4.74 mmol) in EtOH (5 mL) was reacted under microwave condition (140° C.) for 90 min. After cooling to r.t., the mixture was concentrated to dryness. The residue was purified by prep-TLC to give tert-butyl (3S)-3-(hydroxymethyl)-4-[2-hydroxy-2-(6-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate.

Workup

  1. customwas reacted under microwave condition (140° C.) for 90 min
  2. concentrationthe mixture was concentrated to dryness
  3. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-2b9f5cf864de4268a8d8a3d34f96f397
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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