N-Hydroxyphthalimide → (R)-O-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)hydroxylamine

HRID 656571Notes

Reaction equation

HRID 656571 reaction equation
[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([CH2:7][CH2:8][OH:9])[CH2:4][O:3]1.O[N:12]1C(=O)C2C(=CC=CC=2)C1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.O.NN>C(Cl)Cl>[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([CH2:7][CH2:8][O:9][NH2:12])[CH2:4][O:3]1

Participants

7

Reactant 5

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 24654Hydrazine hydrate (1:1)HCID 5363146Diisopropyl azodicarboxylateHCID 11480522(4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 57999095(R)-O-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)hydroxylamineYield 43.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared using the procedure described for Example 2K by using (R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol (4.28 mL, 30 mmol), CH2Cl2 (100 mL), 2-hydroxyisoindolin-1,3-dione (4.9 g, 30 mmol), triphenylphosphine (11.8 g, 45 mmol), diisopropylazodicarboxylate (8.8 ml, 45 mmol) and hydrazine hydrate (6.0 mL, 60 mmol) to afford 2.1 g (43%, over two steps) of (R)—O-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)hydroxylamine (2×) as a pale yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.13 (s, 3H), 1.18 (s, 3H), 1.53-1.71 (m, 2H), 3.53 (m, 2H), 3.79-3.89 (m, 1H), 3.89-4.01 (m, 1H), 4.63-4.81 (m, 1H). MS (ES) [M+H] calculated for C7H16NO3, 162.11. found 162.0.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-7c86be632be74aab9efe6b98fa70fb9d
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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