O-(Tetrahydropyran-2-yl)hydroxylamine → HCID 86638432, compound

HRID 415875Notes

Reaction equation

HRID 415875 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@:14]([OH:19])([CH2:16][O:17][CH3:18])[CH2:13][C@H:12]1[C:20]([OH:22])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:29][NH2:30]>>[OH:19][C@@:14]1([CH2:16][O:17][CH3:18])[CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C@H:12]([C:20](=[O:22])[NH:30][O:29][CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][O:23]2)[CH2:13]1

Participants

3

Reactant 2

HCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 66619671HCID 66619671, compound

Product 1

HCID 86638432HCID 86638432, compoundYield 59%

Procedure

(2S,4R)-Benzyl 4-hydroxy-4-(methoxymethyl)-2-(tetrahydro-2H-pyran-2-yloxycarbamoyl)pyrrolidine-1-carboxylate is prepared from (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxy-4-(methoxymethyl)pyrrolidine-2-carboxylic acid and O-(tetrahydro-2H-pyran-2-yl)hydroxylamine following Method G (yield=59%). 1H NMR (300 MHz, CHCl3) δ 7.57-7.18 (m, 5H), 5.33-5.07 (m, 2H), 4.64-4.45 (m, 1H), 4.09-3.21 (m, 7H), 2.44-1.98 (m, 3H); ESI(+) calcd. for C15H18NO6 (308.11). Found 308.0

Sources & evidence

ORD record
ord-ac92bb62f2ab421586c4429834bc1db9
Source dataset
uspto-grants-2012_01
Patent number
US08088804B2

Reaction notes

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