Boron Trichloride → HCID 640418, compound

HRID 1497296Notes

Reaction equation

C([O:8][C@@H:9]1[C@H:14]2[NH:15][C:16](=[O:18])[O:17][C@H:13]2[CH2:12][C@H:11]([CH2:19][O:20]CC2C=CC=CC=2)[C@H:10]1[O:28]CC1C=CC=CC=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.CO.C(Cl)Cl>C(Cl)Cl>[OH:8][C@@H:9]1[C@H:14]2[NH:15][C:16](=[O:18])[O:17][C@H:13]2[CH2:12][C@H:11]([CH2:19][OH:20])[C@H:10]1[OH:28]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)hexahydrobenzo[d]oxazol-2(3H)-one (7.35 g, 15.5 mmol) in DCM (80 mL) at −78° C. was added a solution of BCl3 in DCM (1.0 M, 53 mL, 53 mmol). The mixture was slowly warmed up to 0° C. and stirred at this temperature for 4 h. The reaction was cooled to −78° C. again and a 1:1 mixture of MeOH-DCM (50 mL) was added dropwise to quench the reaction. Solvents were evaporated and the residue was treated with MeOH for three more times. The crude product was purified by silica gel column chromatography, eluted with 5%-15% MeOH in DCM to give the product of (3aR,4R,5R,6R,7aS)-4,5-dihydroxy-6-(hydroxymethyl)hexahydrobenzo[d]oxazol-2(3H)-one (2.99 g, 95%) as a white solid. 1H NMR (400 MHz, MeOD) δ 4.68-4.71 (m, 1H), 3.72 (dd, J=10.8 Hz, 3.4 Hz, 1H), 3.64 (dd, J=10.8 Hz, 5.2 Hz, 1H), 3.46 (t, J=7.2 Hz, 1H), 3.32 (t, J=8.7 Hz, 1H), 3.19 (t, J=9.4 Hz, 1H), 2.17-2.25 (m, 1H), 1.64-1.75 (m, 2H).

Workup

temperatureThe reaction was cooled to −78° C. again
additionwas added dropwise
customto quench
customthe reaction
customSolvents were evaporated
additionthe residue was treated with MeOH for three more times
customThe crude product was purified by silica gel column chromatography
washeluted with 5%-15% MeOH in DCM

Sources & evidence

ORD record: ord-7a5ec2bf689a4604a9b3f5777a07a665
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199949B2

Reaction notes

Loading…