4-Methylmorpholine → ethyl (3S,4S)-4-amino-3-hydroxy-6-methylheptanoate

HRID 255613Notes

Reaction equation

HRID 255613 reaction equation
Cl.O1CCOCC1.C(OC([NH:15][C@@H:16]([CH2:25][CH:26]([CH3:28])[CH3:27])[C@@H:17]([OH:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=O)(C)(C)C.CN1CCOCC1>CN(C)C=O>[NH2:15][C@@H:16]([CH2:25][CH:26]([CH3:27])[CH3:28])[C@@H:17]([OH:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 11347225ethyl (3S,4S)-4-t-butoxycarbonylamino-3-hydroxy-6-methylheptanoateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 14557507ethyl (3S,4S)-4-amino-3-hydroxy-6-methylheptanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Meanwhile, 5 ml of 6N hydrogen chloride/dioxane were added to 152 mg (0.5 mmole) of ethyl 4(S)-t-butoxycarbonylamino-3(S)-hydroxy-6-methylheptanoate. The solution was stirred for 20 minutes under a nitrogen stream, and then concentrated by evaporation under reduced pressure, to give a solid residue. The resulting residue was dissolved in 2 ml of dimethylformamide, and 0.05 g of N-methylmorpholine was added to give a solution of ethyl 4(S)-amino-3(S)-hydroxy-6-methylheptanoate.

Workup

  1. concentrationconcentrated by evaporation under reduced pressure
  2. customto give a solid residue

Sources & evidence

ORD record
ord-2f0e2971a54d4e49b833add3db059459
Source dataset
uspto-grants-1987_10
Patent number
US04698329

Reaction notes

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