tert-Butyl bromoacetate → Dimethyl (2s,3s,5s)-5-(2-tert-butoxy-2-oxoethoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

HRID 61464Notes

Reaction equation

HRID 61464 reaction equation
[OH:1][C@@H:2]1[CH2:7][N:6]([C:8]([O:10][CH3:11])=[O:9])[C@H:5]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[C@@H:4]([C:26]([O:28][CH3:29])=[O:27])[CH2:3]1.CC(C)([O-])C.[K+].[CH3:36][C:37]([O:40][C:41](=[O:44])[CH2:42]Br)([CH3:39])[CH3:38]>O1CCCC1>[C:37]([O:40][C:41](=[O:44])[CH2:42][O:1][C@@H:2]1[CH2:7][N:6]([C:8]([O:10][CH3:11])=[O:9])[C@H:5]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[C@@H:4]([C:26]([O:28][CH3:29])=[O:27])[CH2:3]1)([CH3:39])([CH3:38])[CH3:36]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 67304346dimethyl(2S,3S,5S)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Product 1

HCID 67303979Dimethyl (2s,3s,5s)-5-(2-tert-butoxy-2-oxoethoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of dimethyl(2S,3S,5S)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate (50.0 mg, 0.000123 mol) in tetrahydrofuran (0.50 mL, 0.0062 mol) was added 1.00 M of potassium tert-butoxide in tetrahydrofuran (0.150 mL). After stirred at rt for 30 min, to the mixture was added bromo-acetic acid 1,1-dimethylethyl ester (0.0228 mL, 0.000154 mol). The resulting mixture was stirred at rt overnight and then concentrated to dry.

Workup

  1. stirringThe resulting mixture was stirred at rt overnight
  2. concentrationconcentrated
  3. customto dry

Sources & evidence

ORD record
ord-49b234f9b422415a9b2b2e56258cad61
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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