Triethylamine → HCID 66953120, compound

HRID 723487Notes

Reaction equation

HRID 723487 reaction equation
N[C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[OH:15].CCN(CC)CC.[C:23](ON1C(=O)CCC1=O)([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C(Cl)Cl.CCOC(C)=O>[CH2:26]([O:25][C:23]([C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@@H:3]1[OH:15])=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 10727458rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate

Product 1

HCID 66953120HCID 66953120, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of Compound 249A (1.40 g, 6.47 mmoL) in 10 mL of CH2Cl2 was added Et3N (1.08 mL, 7.76 mmoL), followed by Cbz-OSu (1.69 g, 6.80 mmoL). The reaction mixture was stirred at room temperature for 16 hrs and then diluted with 300 mL of EtOAc. The organic layer was washed with 5% citric acid solution (2×40 mL), 5% K2CO3 solution (2×40 mL) and brine (40 mL) and dried (MgSO4). The residue was filtered and concentrated in vacuo to afford 2.25 g (yield: 99%) of Compound 262A. It had an analytical HPLC retention time=3.02 min. (Phenomenox S5 C18-HC 4.6×50 mm column, 10–90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 ml/min, monitoring at 220 nm) and a LC/MS M++1=351.

Workup

  1. washThe organic layer was washed with 5% citric acid solution (2×40 mL), 5% K2CO3 solution (2×40 mL) and brine (40 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationThe residue was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2601f50dafc4d7caee23ce10f682fc3
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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