Hydrochloric Acid → HCID 86753270, compound

HRID 400223Notes

Reaction equation

[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:15][CH2:14][CH2:13][C@@:12]2([CH3:16])[C@H:8]1[CH2:9][CH2:10][C@@H:11]2[C@@H:17]([CH3:20])[CH2:18][OH:19])([CH3:4])([CH3:3])[CH3:2].[C:23](Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25].Cl>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:15][CH2:14][CH2:13][C@@:12]2([CH3:16])[C@H:8]1[CH2:9][CH2:10][C@@H:11]2[C@@H:17]([CH3:20])[CH2:18][O:19][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

198 mg (0,606 mmol) of (R)-2-[(1R,3aR,4S,7aR)-4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-propan-1-ol was dissolved in pyridine (3 ml) and cooled to 0° C. DMAP (18,5 mg; 0,152 mmol) was added followed by a slow addition of pivaloyl-chloride (97 ml; 0,79 mmol). The mixture was allowed to react for half an hour at 0° C. and half an hour at room temperature. The reaction mixture was poured in a cold aqueous HCl (25%) solution. Extraction with ether, washing with brine, drying over Na2 SO4 and solvent removal gave a dark oil which was purified by column chromatography on silica gel (eluent: n-hexane/ethyl-acetate 97:3) affording 215 mg (86,3%) of 2,2-Dimethyl-propionic acid (R)-2-[(1R,3aR,4S,7aR)-4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-propyl ester (J1) as a yellow oil.

Workup

customto react for half an hour at 0° C. and half an hour at room temperature
extractionExtraction with ether
washwashing with brine
customdrying over Na2 SO4 and solvent removal
customgave a dark oil which
customwas purified by column chromatography on silica gel (eluent: n-hexane/ethyl-acetate 97:3)

Sources & evidence

ORD record: ord-a961d0ca68e64cf9843be1250bd2be3f
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05827883

Reaction notes

Loading…