N-Hydroxyphthalimide → HCID 57998935, compound

HRID 656572Notes

Reaction equation

HRID 656572 reaction equation
[CH3:1][O:2][CH:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([CH2:13][OH:14])[O:4]1.O[N:16]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][O:2][CH:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([CH2:13][O:14][NH2:16])[O:4]1

Participants

7

Reactant 5

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 24654Hydrazine hydrate (1:1)HCID 5363146Diisopropyl azodicarboxylateHCID 11447040Methyl-2,3-O-isopropylidene-D-ribofuranoside

Product 1

HCID 57998935HCID 57998935, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared using the procedure described for Example 2K by using ((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (2.04 g, 10 mmol), CH2Cl2 (25 mL), 2-hydroxyisoindolin-1,3-dione (2.0 g, 12 mmol), triphenylphosphine (4.0 g, 15 mmol), diisopropylazodicarboxylate (3.0 ml, 15 mmol) and hydrazine hydrate (2.0 mL, 20 mmol) to afford 1.12 g of O-(((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)hydroxylamine (2Y) (50%, over two steps) as a pale yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.24 (s, 3H) 1.26 (s, 3H) 3.31 (s, 3H) 3.59-3.75 (m, 2H) 4.44 (t, J=7.20 Hz, 1H) 4.56 (d, J=5.81 Hz, 1H) 4.67 (d, J=6.06 Hz, 1H) 4.92-5.00 (m, 1H). MS (ES) [M+H] calculated for C9H18NO5, 220.11. found 220.10.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-ea512e9cd15548ceb0183cb33ce661fc
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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