Trifluoroacetic acid → 2(S)-(2(R)-Hydroxypropyl)piperazine

HRID 131404Notes

Reaction equation

HRID 131404 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][C@@H:9]1[CH2:21][C@@H:22]([OH:24])[CH3:23])=O)(C)(C)C.C(OC(N1CCN(C(OC(C)(C)C)=O)C[C@@H]1C[C@H](O)C)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[OH:24][C@H:22]([CH3:23])[CH2:21][C@H:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:8]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 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 ester

Product 1

HCID 552988912(S)-(2(R)-Hydroxypropyl)piperazineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 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 (5.11 g, 14.8 mmol) in dichloromethane (100 mL) stirring at 0° C., add trifluoroacetic acid (25 mL). Warm the mixture to room temperature and stir. After 18 hours evaporate to a yellow oil. Dilute the mixture with methanol and apply to a 60 g SCX column. Wash with methanol and elute with 2N ammonia in methanol to obtain the title compound (mixture of diastereoisomers) as an oil (1.932 g, 90%): mass spectrum (APCI): m/z =145.1 (M+1).

Workup

  1. customAfter 18 hours evaporate to a yellow oil
  2. additionDilute the mixture with methanol
  3. washWash with methanol
  4. washelute with 2N ammonia in methanol

Sources & evidence

ORD record
ord-b089698e83c64e7982efce2c3395df57
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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