Tetrahydrofuran → N-Acetyl dihydrosphingosine

HRID 222838Notes

Reaction equation

C1COCC1.[BH4-].[Na+].[C:8]([NH:11][C@H:12]([C@H:18]([OH:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:13](OCC)=[O:14])(=[O:10])[CH3:9].C(OCC)(=O)C>O>[C:8]([NH:11][C@H:12]([C@H:18]([OH:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:13][OH:14])(=[O:10])[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

A THF suspension (0.3 mL) containing sodium borohydride (38.2 mg, 0.93 mmol) was heated to 60° C., and a THF solution (2.5 mL) of ethyl (2R,3R)-2-acetylamino-3-hydroxyoctadecanoate (250.1 mg. 0.62 mmol) synthesized in the same manner as Example 14 was added thereto dropwise for 5.5 hours. After completion of the dropwise addition, the mixture was further stirred at 60° C. for 17 hours. After ethyl acetate and water were added thereto, the reaction mixture was stirred at 60° C. for 1 hour. After the organic layer was separated, the organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was removed in reduced pressure. It was confirmed that 178.7 mg of the title compound was contained (yield: 84%). HPLC analysis was carried out to find that the optical purity of the anti-form was 99% ee.

Workup

additionwas added
additionAfter completion of the dropwise addition
stirringthe reaction mixture was stirred at 60° C. for 1 hour
customAfter the organic layer was separated
washthe organic layer was washed with saturated brine
dry with materialdried with magnesium sulfate
customThe solvent was removed in reduced pressure

Sources & evidence

ORD record: ord-f2baead9609d4f84b39619e6d1d61a41
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207370B2

Reaction notes

Loading…