1,4-Bis(tert-butoxycarbonyl)-2-formylmethylpiperazine → 2(S)-(2(R)-hydroxypropyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester

HRID 131403Notes

Reaction equation

HRID 131403 reaction equation
[CH3:1][Mg]Br.[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[CH2:24][CH:25]=[O:26])=[O:10])([CH3:7])([CH3:6])[CH3:5]>O1CCCC1.[Cl-].[NH4+]>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C@@H:12]1[CH2:24][C@@H:25]([OH:26])[CH3:1])=[O:10])([CH3:7])([CH3:6])[CH3:5].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C@@H:12]1[CH2:24][C@H:25]([OH:26])[CH3:1])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 2

HCID 227100181,4-Bis(tert-butoxycarbonyl)-2-formylmethylpiperazineHCID 178418573HCID 178418573, compound

Product 2

HCID 692097632(S)-(2(S)-hydroxypropyl)piperazine-1,4-dicarboxylic acid di-tert-butyl esterHCID 692116212(S)-(2(R)-hydroxypropyl)piperazine-1,4-dicarboxylic acid di-tert-butyl esterYield 198.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Add methylmagnesium bromide (3.61 mL, 10.8 mmol, 3M solution in diethyl ether) to a solution of 2-(2-oxoethyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester (3.036 g, 9.84 mmol) in tetrahydrofuran (30 mL) at 0° C. Warm the mixture to room temperature and stir for 5 hours. Dilute the mixture with saturated ammonium chloride and extract three times with ethyl acetate. Combine the organic layers, dry over sodium sulfate and concentrate under reduced pressure to give 2(S)-(2(S)-hydroxypropyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester and 2(S)-(2(R)-hydroxypropyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester (3.37 g, 99%) as a yellow oily solid: mass spectrum (APCI): m/z=245.2 (M+1-BOC).

Workup

  1. extractionextract three times with ethyl acetate
  2. dry with materialdry over sodium sulfate
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-5335de4fa1ff4b5ba2cdef4cdf448ddb
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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