tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylate → HCID 86727083, compound

HRID 1502051Notes

Reaction equation

HRID 1502051 reaction equation
[Cl: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].[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>C(O)C>[Cl:1][C:2]1[C:3]([C:4]#[N:5])=[C:6]([F:13])[CH:7]=[CH:8][C:9]=1[CH:10]([OH:11])[CH2:12][N:21]1[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]1[CH2:15][OH:14]

Participants

4

Reactant 2

HCID 24820286tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 867270822-Chloro-6-fluoro-3-(oxiran-2-yl)benzonitrile

Product 1

HCID 86727083HCID 86727083, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-6-fluoro-3-(oxiran-2-yl)benzonitrile (9.1 g, 46 mmol) and (R)-tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate (14.9 g, 69.1 mmol) were dissolved in ethanol (105 mL) and dispensed into 9 sealed tubes then microwaved at 140° C. for 1 h. The combined reaction mixture was concentrated and purified through a 330 g ISCO Redi-sep column with 50%-100 ethyl acetate/hexane solvent system to yield the title compound.

Workup

  1. customthen microwaved at 140° C. for 1 h
  2. customThe combined reaction mixture
  3. concentrationwas concentrated
  4. custompurified through a 330 g ISCO Redi-sep column with 50%-100 ethyl acetate/hexane solvent system

Sources & evidence

ORD record
ord-66e524559e994221b41cd435c33fd29e
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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