Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 18429039, compound

HRID 1279750Notes

Reaction equation

HRID 1279750 reaction equation
Cl.CN[O:4][CH3:5].[CH3:6][CH:7]([CH:23]([OH:27])[CH:24]([CH3:26])[CH3:25])[C:8]([N:10]1[C@@H:14](CC2C=CC=CC=2)COC1=[Se])=[O:9]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[OH:27][CH:23]([CH:24]([CH3:25])[CH3:26])[CH:7]([CH3:6])[C:8]([N:10]([O:4][CH3:5])[CH3:14])=[O:9]

Participants

5

Reactant 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 23378955HCID 23378955, compound

Product 1

HCID 18429039HCID 18429039, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N,O-Dimethylhydroxyl-amine hydrochloride (380 mg, 3.90 mmol) and 4-dimethylaminopyridine (244 mg, 2.00 mmol) was added to a solution of (4S)-3-(2,4-dimethyl-3-hydroxyl-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidineselone (616 mg, 2.00 mmol) in CH2Cl2 (10 mL). The resulting solution was stirred at room temperature for 4 days. The solvent was removed under reduced pressure. Purification of the residue by silica gel column chromatography (CH2Cl2/ether; 95/5; v/v) afforded 210 mg (55%) of 3-hydroxy-N-methoxy-N,2,4-trimethyl-pentanamide. 1H NMR δ 3.94 (br s, 1H), 3.72 (s, 3H), 3.45 (dd, 1H, J=8.4 Hz, J=2.1 Hz), 3.21 (s, 3H), 3.10 (br m, 1H), 1.73 (m, 1H), 1.16 (d, 3H, J=7.1 Hz), 1.04 (d, 3H, J=6.6 Hz), 0.88 (d, 3H, J=6.8 Hz); 13C NMR δ 178.48, 76.90, 61.48, 35.72, 31.88, 30.20, 19.16, 18.90, 9.90

Workup

  1. customThe solvent was removed under reduced pressure
  2. customPurification of the residue by silica gel column chromatography (CH2Cl2/ether; 95/5; v/v)

Sources & evidence

ORD record
ord-a06e4fe7ecdb46d088546810d56c08d9
Source dataset
uspto-grants-2002_09
Patent number
US06448409B1

Reaction notes

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