4-Methylmorpholine → HCID 70002522, compound

HRID 1264415Notes

Reaction equation

HRID 1264415 reaction equation
[C:1]([N:8]1[CH2:16][C@H:14]([OH:15])[CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.CN1CCOCC1.[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C>C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:16][C@H:14]([OH:15])[CH2:13][C@H:9]1[C:10]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:12])=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 8082PiperidineHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium Tetrafluoroborate

Product 1

HCID 70002522HCID 70002522, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.0 g (17.3 mmol) N-BOC-L-hydroxy-proline in 150 ml CH2Cl2 were treated with 1.71 ml (17.3 mmol) piperidine, 1.9 ml (17.2 mmol) NMM and 6.16 g (20.7 mmol) TPTU at RT over night. The mixture was washed with 1M KHSO4, water, 5% aq. NaHCO3 solution, water and brine, dried over Na2SO4 and was concentrated. Column chromatography yielded 3.87 g (75%) (2S,4R)-4-Hydroxy-2-(piperidin-1-ylcarbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as white solid, MS: 298 (M).

Workup

  1. washThe mixture was washed with 1M KHSO4, water, 5% aq. NaHCO3 solution, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-28d182fbfd98409cba3778a345c35da6
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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