Borane;tetrahydrofuran → HCID 52913601, compound

HRID 1944104Notes

Reaction equation

HRID 1944104 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([O:17][C:18](=[O:20])[CH3:19])[C:8]2([CH2:10][CH2:9]2)[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]3[O:37][CH2:36][C:35](=O)[NH:34][C:33]=3[CH:39]=2)[CH:22]=1)(=[O:3])[CH3:2].B.C1COCC1>C1COCC1>[C:1]([O:4][C@@H:5]1[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([O:17][C:18](=[O:20])[CH3:19])[C:8]2([CH2:10][CH2:9]2)[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]3[O:37][CH2:36][CH2:35][NH:34][C:33]=3[CH:39]=2)[CH:22]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 52913600HCID 52913600, compound

Product 1

HCID 52913601HCID 52913601, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of acetic acid (5S,6S,7R,8S)-6,7-diacetoxy-5-[4-chloro-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-4-oxa-spiro[2.5]oct-8-yl ester (100 mg, 0.18 mmol) in THF (6 mL) was added a solution of BH3-THF (2.2 ml, 1.8 mmol) and heated to reflux overnight. Reaction was quenched with the addition of ethyl acetate. The solvent was evaporated and the crude product was purified by silica gel column chromatography to furnish the acetic acid (5S,6S,7R,8S)-6,7-diacetoxy-5-[4-chloro-3-(3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-4-oxa-spiro[2.5]oct-8-yl ester (56 mg).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customReaction
  4. customwas quenched with the addition of ethyl acetate
  5. customThe solvent was evaporated
  6. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3e84d0ed0bf241e3af3138f725f5571c
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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