Hydroxylamine → HCID 9816024, compound

HRID 1830963Notes

Reaction equation

HRID 1830963 reaction equation
C(OC([N:11]1C[C@H](O)C[C@H]1C(O)=O)=O)C1C=CC=CC=1.C(O[C:28]1[C:47]([O:48][CH3:49])=[CH:46][C:31]([C:32]([N:34]2[CH:38]=[C:37](CC(OC)=O)[CH2:36][C@H:35]2[CH2:44]O)=[O:33])=[C:30]([N+]([O-])=O)[CH:29]=1)C1C=CC=CC=1.NO.[N+](O)([O-])=O>C(Cl)(Cl)Cl>[CH3:49][O:48][C:47]1[C:46]2[N:11]=[CH:44][C@@H:35]3[CH2:36][CH2:37][CH2:38][N:34]3[C:32](=[O:33])[C:31]=2[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 944Nitric Acid2×HCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate2×HCID 69621453HCID 69621453, compound2×

Product 1

HCID 9816024HCID 9816024, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Finely ground Cd/Pb couple (1.02 g). was added in small portions to a stirred solution of 100 (0.64 g, 1.51 mmol) in THF (10 mL) and 1M NH4OAc (10 mL). The reaction was followed by TLC (EtOAc), when no more starting material was observed, the mixture was poured into ethyl acetate (200 mL). The organic phase was dried over MgSO4 and evaporated to yield the product as a pale yellow oil (0.28 g, 80%): 1H NMR (270 MHz, CDCl3) δ2.15 (m, 4H); 3.52 (m, 2H); 3.87 (s, 3H); 5.15 (m, 1H); 6.8-7.2 (m, 3H); 7.8 (d, J=4.7 Hz, 1H, imine H11). IR (Nujol): cm−1 3373, 2975, 1621, 1576, 1440, 1419, 1250, 1075, 750. MS: m/e (relative intensity) 230 (M+., 100), 215 (45), 201 (20), 187 (5), 160 (5), 146 (4), 133 (20), 105 (10), 76 (25), 70 (45), 63 (3), 51 (3). HRMS Calculated for C13H14N2O2: 230.1055. Found: 230.1055. [α]25D=+455.3° (c=0.6, CHCl3).

Sources & evidence

ORD record
ord-f34232a4476a45e9abcf0af938b34ace
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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